ZA200306991B - Anthranilic acid amides, method for the production thereof, their use as antiarrhythmia agents, and pharmaceutical preparations thereof. - Google Patents
Anthranilic acid amides, method for the production thereof, their use as antiarrhythmia agents, and pharmaceutical preparations thereof. Download PDFInfo
- Publication number
- ZA200306991B ZA200306991B ZA200306991A ZA200306991A ZA200306991B ZA 200306991 B ZA200306991 B ZA 200306991B ZA 200306991 A ZA200306991 A ZA 200306991A ZA 200306991 A ZA200306991 A ZA 200306991A ZA 200306991 B ZA200306991 B ZA 200306991B
- Authority
- ZA
- South Africa
- Prior art keywords
- carbon atoms
- alkyl
- ocf3
- alkoxy
- come
- Prior art date
Links
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 4
- 239000003416 antiarrhythmic agent Substances 0.000 title description 11
- PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical class NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 title description 3
- 238000000034 method Methods 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims description 170
- 125000000217 alkyl group Chemical group 0.000 claims description 95
- -1 dimethyl- amino, sulfamoyl Chemical group 0.000 claims description 78
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 47
- 229910052739 hydrogen Inorganic materials 0.000 claims description 46
- 239000001257 hydrogen Substances 0.000 claims description 46
- 125000003545 alkoxy group Chemical group 0.000 claims description 44
- 125000003118 aryl group Chemical group 0.000 claims description 42
- 125000001072 heteroaryl group Chemical group 0.000 claims description 42
- 150000001875 compounds Chemical class 0.000 claims description 40
- 125000001424 substituent group Chemical group 0.000 claims description 39
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 36
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 33
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 33
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
- 150000002431 hydrogen Chemical class 0.000 claims description 19
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 239000001301 oxygen Substances 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 125000004076 pyridyl group Chemical group 0.000 claims description 14
- 206010003658 Atrial Fibrillation Diseases 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 11
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 230000000694 effects Effects 0.000 claims description 7
- 238000011321 prophylaxis Methods 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 6
- 206010003119 arrhythmia Diseases 0.000 claims description 6
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 6
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 6
- 108091006146 Channels Proteins 0.000 claims description 4
- 230000036982 action potential Effects 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 206010042600 Supraventricular arrhythmias Diseases 0.000 claims description 3
- 230000006793 arrhythmia Effects 0.000 claims description 3
- 230000001746 atrial effect Effects 0.000 claims description 3
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- 239000000654 additive Substances 0.000 claims 3
- 239000003937 drug carrier Substances 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 239000002876 beta blocker Substances 0.000 claims 1
- 229940097320 beta blocking agent Drugs 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 230000000144 pharmacologic effect Effects 0.000 claims 1
- 230000003288 anthiarrhythmic effect Effects 0.000 description 9
- 101001026214 Homo sapiens Potassium voltage-gated channel subfamily A member 5 Proteins 0.000 description 7
- 230000003213 activating effect Effects 0.000 description 5
- 230000003111 delayed effect Effects 0.000 description 5
- 206010003662 Atrial flutter Diseases 0.000 description 4
- 210000002837 heart atrium Anatomy 0.000 description 4
- 206010003130 Arrhythmia supraventricular Diseases 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 102000004257 Potassium Channel Human genes 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 108020001213 potassium channel Proteins 0.000 description 3
- 230000001536 pro-arrhythmogenic effect Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000002651 drug therapy Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000013178 mathematical model Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000036279 refractory period Effects 0.000 description 2
- 210000001567 regular cardiac muscle cell of ventricle Anatomy 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 230000033764 rhythmic process Effects 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- WYLSNVABSFSWOS-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinolino[2,1-d][1,4]benzodiazepine Chemical class C1=CN=C2CCCCC2=C2C3=CC=CC=C3C=CN21 WYLSNVABSFSWOS-UHFFFAOYSA-N 0.000 description 1
- JRZGPXSSNPTNMA-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalen-1-amine Chemical class C1=CC=C2C(N)CCCC2=C1 JRZGPXSSNPTNMA-UHFFFAOYSA-N 0.000 description 1
- LEBVLXFERQHONN-UHFFFAOYSA-N 1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide Chemical compound CCCCN1CCCCC1C(=O)NC1=C(C)C=CC=C1C LEBVLXFERQHONN-UHFFFAOYSA-N 0.000 description 1
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 description 1
- XJEVHMGJSYVQBQ-UHFFFAOYSA-N 2,3-dihydro-1h-inden-1-amine Chemical class C1=CC=C2C(N)CCC2=C1 XJEVHMGJSYVQBQ-UHFFFAOYSA-N 0.000 description 1
- ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 208000032845 Atrial Remodeling Diseases 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 108010042111 Kv1.5 Potassium Channel Proteins 0.000 description 1
- 102000004425 Kv1.5 Potassium Channel Human genes 0.000 description 1
- 208000001871 Tachycardia Diseases 0.000 description 1
- 208000018452 Torsade de pointes Diseases 0.000 description 1
- 208000002363 Torsades de Pointes Diseases 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 210000002072 atrial myocyte Anatomy 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 229960003150 bupivacaine Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 206010061592 cardiac fibrillation Diseases 0.000 description 1
- 229940082638 cardiac stimulant phosphodiesterase inhibitors Drugs 0.000 description 1
- 238000013194 cardioversion Methods 0.000 description 1
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 description 1
- 229960002986 dinoprostone Drugs 0.000 description 1
- 229960002994 dofetilide Drugs 0.000 description 1
- IXTMWRCNAAVVAI-UHFFFAOYSA-N dofetilide Chemical compound C=1C=C(NS(C)(=O)=O)C=CC=1CCN(C)CCOC1=CC=C(NS(C)(=O)=O)C=C1 IXTMWRCNAAVVAI-UHFFFAOYSA-N 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 230000002600 fibrillogenic effect Effects 0.000 description 1
- 210000005003 heart tissue Anatomy 0.000 description 1
- 229960003444 immunosuppressant agent Drugs 0.000 description 1
- 239000003018 immunosuppressive agent Substances 0.000 description 1
- 230000000415 inactivating effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 230000002107 myocardial effect Effects 0.000 description 1
- 208000031225 myocardial ischemia Diseases 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 239000002571 phosphodiesterase inhibitor Substances 0.000 description 1
- 239000003450 potassium channel blocker Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 1
- 208000002815 pulmonary hypertension Diseases 0.000 description 1
- 230000002336 repolarization Effects 0.000 description 1
- 239000003001 serine protease inhibitor Substances 0.000 description 1
- GZKLJWGUPQBVJQ-UHFFFAOYSA-N sertindole Chemical compound C1=CC(F)=CC=C1N1C2=CC=C(Cl)C=C2C(C2CCN(CCN3C(NCC3)=O)CC2)=C1 GZKLJWGUPQBVJQ-UHFFFAOYSA-N 0.000 description 1
- 229960000652 sertindole Drugs 0.000 description 1
- 229960002370 sotalol Drugs 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- CTIRHWCPXYGDGF-HDICACEKSA-N tedisamil Chemical compound [H][C@]12CN(CC3CC3)C[C@]([H])(CN(CC3CC3)C1)C21CCCC1 CTIRHWCPXYGDGF-HDICACEKSA-N 0.000 description 1
- 229960002926 tedisamil Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/335—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/08—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/21—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
- C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
- C07C311/38—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton
- C07C311/44—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/40—Acylated substituent nitrogen atom
-
- 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
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D231/16—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/14—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/28—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/14—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Heart & Thoracic Surgery (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)
- Quinoline Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Indole Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10121003A DE10121003A1 (de) | 2001-04-28 | 2001-04-28 | Anthranilsäureamide, Verfahren zur Herstellung, ihrer Verwendung als Medikament sowie sie enthaltende pharmazeutische Zubereitungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200306991B true ZA200306991B (en) | 2004-08-31 |
Family
ID=7683152
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200306991A ZA200306991B (en) | 2001-04-28 | 2003-09-08 | Anthranilic acid amides, method for the production thereof, their use as antiarrhythmia agents, and pharmaceutical preparations thereof. |
Country Status (36)
| Country | Link |
|---|---|
| US (2) | US7235690B2 (zh) |
| EP (1) | EP1385820B1 (zh) |
| JP (1) | JP4231295B2 (zh) |
| KR (1) | KR100865250B1 (zh) |
| CN (1) | CN100522937C (zh) |
| AR (1) | AR033623A1 (zh) |
| AT (1) | ATE528288T1 (zh) |
| AU (1) | AU2002338494B2 (zh) |
| BG (1) | BG108215A (zh) |
| BR (1) | BR0209185A (zh) |
| CA (1) | CA2445341C (zh) |
| CR (1) | CR7099A (zh) |
| CZ (1) | CZ20032921A3 (zh) |
| DE (1) | DE10121003A1 (zh) |
| EC (1) | ECSP034780A (zh) |
| EE (1) | EE05267B1 (zh) |
| HK (1) | HK1064663A1 (zh) |
| HR (1) | HRP20030871A2 (zh) |
| HU (1) | HUP0304043A3 (zh) |
| IL (2) | IL158504A0 (zh) |
| MA (1) | MA27002A1 (zh) |
| MX (1) | MXPA03008419A (zh) |
| MY (1) | MY143521A (zh) |
| NO (1) | NO328872B1 (zh) |
| NZ (1) | NZ529129A (zh) |
| OA (1) | OA12598A (zh) |
| PE (1) | PE20021088A1 (zh) |
| PL (1) | PL363433A1 (zh) |
| RS (1) | RS82003A (zh) |
| RU (1) | RU2283833C2 (zh) |
| SK (1) | SK13262003A3 (zh) |
| TN (1) | TNSN03084A1 (zh) |
| TW (1) | TWI259833B (zh) |
| UA (1) | UA76986C2 (zh) |
| WO (1) | WO2002088073A1 (zh) |
| ZA (1) | ZA200306991B (zh) |
Families Citing this family (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7119120B2 (en) * | 2001-12-26 | 2006-10-10 | Genzyme Corporation | Phosphate transport inhibitors |
| US7119112B2 (en) * | 2002-02-28 | 2006-10-10 | Icagen, Inc. | Sulfonamides as potassium channel blockers |
| CN1659142A (zh) * | 2002-04-26 | 2005-08-24 | 石原产业株式会社 | 吡啶化合物或其盐和含有它们的除草剂 |
| DE10312061A1 (de) * | 2003-03-18 | 2004-09-30 | Aventis Pharma Deutschland Gmbh | Kombination von Phenylcarbonsäureamiden mit Blockern des IK-Kanals und deren Verwendung zur Behandlung von Vorhofarrhythmien |
| US20040192738A1 (en) * | 2003-03-18 | 2004-09-30 | Aventis Pharma Deutschland Gmbh | 2-(Butyl-1-sulfonylamino)-N-[1(R)-(6-methoxypyridin-3-yl)propyl] benzamide, its use as a medicament, and pharmaceutical preparations comprising it |
| DE10312073A1 (de) * | 2003-03-18 | 2004-09-30 | Aventis Pharma Deutschland Gmbh | 2-(Butyl-1-sulfonylamino)-N-[1(R)-(6-methoxy-pyridin-3yl)-propyl]-benzamid, dessen Verwendung als Medikament sowie dieses enthaltende pharmazeutische Zubereitungen |
| GB0315950D0 (en) | 2003-06-11 | 2003-08-13 | Xention Discovery Ltd | Compounds |
| DE602004004663T2 (de) | 2003-08-08 | 2007-11-22 | Janssen Pharmaceutica N.V. | Verfahren zur herstellung von 2- (chinoxalin-5-ylsulfonylamino) -benzamid-verbindungen |
| DE10341233A1 (de) * | 2003-09-08 | 2005-03-24 | Aventis Pharma Deutschland Gmbh | Kombination von Phenylcarbonsäureamiden mit beta-Adrenozeptoren-Blockern und deren Verwendung zur Behandlung von Vorhofarrhythmien |
| DE102004009931A1 (de) * | 2004-02-26 | 2005-09-15 | Aventis Pharma Deutschland Gmbh | Kv1.5-Blocker zur selektiven Steigerung der Vorhofkontraktilität und Behandlung der Herzinsuffizienz |
| GB0412986D0 (en) | 2004-06-10 | 2004-07-14 | Xention Discovery Ltd | Compounds |
| KR20070057252A (ko) * | 2004-09-24 | 2007-06-04 | 얀센 파마슈티카 엔.브이. | 설폰아미드 화합물 |
| US7576212B2 (en) | 2004-12-09 | 2009-08-18 | Xention Limited | Thieno[2,3-B] pyridines as potassium channel inhibitors |
| GB0525164D0 (en) | 2005-12-09 | 2006-01-18 | Xention Discovery Ltd | Compounds |
| GB0526252D0 (en) * | 2005-12-22 | 2006-02-01 | Novartis Ag | Organic compounds |
| GB2434794A (en) * | 2006-02-03 | 2007-08-08 | Prom Ltd | Continuous process for forming anthranilic acid and treatment of waste water containing organic material |
| US7678818B2 (en) * | 2006-02-07 | 2010-03-16 | Hoffmann-La Roche Inc. | Anthranilamide and 2-amino-heteroarene-carboxamide compounds |
| JP5161871B2 (ja) * | 2006-04-27 | 2013-03-13 | サノフィ−アベンティス・ドイチュラント・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | Ｔａｓｋ−１およびｔａｓｋ−３イオンチャンネルの阻害剤 |
| EP2303013A1 (en) * | 2008-07-07 | 2011-04-06 | Fasgen, Inc. | Novel compounds, pharmaceutical compositions containing same, methods of use for same, and methods for preparing same |
| GB0815781D0 (en) | 2008-08-29 | 2008-10-08 | Xention Ltd | Novel potassium channel blockers |
| GB0815782D0 (en) | 2008-08-29 | 2008-10-08 | Xention Ltd | Novel potassium channel blockers |
| GB0815784D0 (en) | 2008-08-29 | 2008-10-08 | Xention Ltd | Novel potassium channel blockers |
| GB201105659D0 (en) | 2011-04-01 | 2011-05-18 | Xention Ltd | Compounds |
| AU2012272898A1 (en) | 2011-06-24 | 2013-04-11 | Amgen Inc. | TRPM8 antagonists and their use in treatments |
| US8710043B2 (en) | 2011-06-24 | 2014-04-29 | Amgen Inc. | TRPM8 antagonists and their use in treatments |
| NO3175985T3 (zh) | 2011-07-01 | 2018-04-28 | ||
| US20150045305A1 (en) | 2012-01-27 | 2015-02-12 | Gilead Sciences, Inc. | Combination therapies using late sodium ion channel blockers and potassium ion channel blockers |
| US8952009B2 (en) | 2012-08-06 | 2015-02-10 | Amgen Inc. | Chroman derivatives as TRPM8 inhibitors |
| CN103130696B (zh) * | 2013-03-21 | 2014-06-11 | 山东大学 | 邻氨基苯甲酰胺类化合物及其制备方法与应用 |
| CA2959208C (en) | 2014-08-29 | 2023-09-19 | Tes Pharma S.R.L. | Pyrimidine derivatives and their use as inhibitors of alpha-amino-beta-carboxymuconate-epsilon-semialdehyde decarboxylase |
| KR101893836B1 (ko) | 2016-07-11 | 2018-08-31 | 김종해 | 식물성 대체 우유 제조 방법과 시스템 |
| WO2020070049A1 (en) | 2018-10-02 | 2020-04-09 | Syngenta Participations Ag | Pesticidally active benzene- and azine-amide compounds |
| CN111285806B (zh) * | 2018-12-06 | 2022-04-15 | 中国医学科学院药物研究所 | 吡唑类化合物及其制备方法、用途和药物组合物 |
| UY38623A (es) | 2019-03-29 | 2020-10-30 | Syngenta Crop Protection Ag | Compuestos de diazina-amida activos como pesticidas |
| MX2021012162A (es) | 2019-04-05 | 2021-11-03 | Syngenta Crop Protection Ag | Compuestos de diazina-amida activos como pesticidas. |
| JOP20210273A1 (ar) | 2019-04-11 | 2023-01-30 | Syngenta Crop Protection Ag | مركبات دايازين - أميد نشطة بشكل مبيد للآفات |
| BR112022003375A2 (pt) | 2019-08-23 | 2022-05-17 | Syngenta Crop Protection Ag | Compostos de pirazina-amida pesticidamente ativos |
| PE20221765A1 (es) | 2019-11-01 | 2022-11-11 | Syngenta Crop Protection Ag | Compuestos heteroaromaticos biciclicos condensados activos como pesticidas |
| WO2021151926A1 (en) | 2020-01-30 | 2021-08-05 | Syngenta Crop Protection Ag | Pesticidally active fused bicyclic heteroaromatic amino compounds |
| WO2021170881A1 (en) | 2020-02-27 | 2021-09-02 | Syngenta Crop Protection Ag | Pesticidally active diazine-bisamide compounds |
| WO2022101265A1 (en) | 2020-11-13 | 2022-05-19 | Syngenta Crop Protection Ag | Pesticidally active fused bicyclic heteroaromatic compounds |
| JP2024524883A (ja) | 2021-06-09 | 2024-07-09 | シンジェンタ クロップ プロテクション アクチェンゲゼルシャフト | 殺有害生物的に活性なジアジン－アミド化合物 |
| MX2024000075A (es) | 2021-06-24 | 2024-02-23 | Syngenta Crop Protection Ag | Derivados de 2-[3-[1 [(quinazolin-4-il)amino]etil]pirazin-2-il]tia zol-5-carbonitrilo y compuestos similares como pesticidas. |
| CA3224710A1 (en) | 2021-07-29 | 2023-02-02 | Thomas Pitterna | Pesticidally active fused bicyclic heteroaromatic compounds |
| CN118265707A (zh) | 2021-10-27 | 2024-06-28 | 先正达农作物保护股份公司 | 杀有害生物活性的哒嗪酮化合物 |
| WO2023104714A1 (en) | 2021-12-10 | 2023-06-15 | Syngenta Crop Protection Ag | Pesticidally active pyridazinone compounds |
| WO2023247360A1 (en) | 2022-06-21 | 2023-12-28 | Syngenta Crop Protection Ag | Pesticidally active fused bicyclic heteroaromatic compounds |
| WO2024110554A1 (en) | 2022-11-23 | 2024-05-30 | Syngenta Crop Protection Ag | N-[(1 -[2-[6-(pyridazin-3-yl]-1,2,4-triazol-3-yl]ethyl]-quinazolin-4-amine and n-[1-[3-(6-(pyridazin-3-yl)pyrazin-2-yl]ethyl]-8-quinazolin-4-amine derivatives as pesticides |
| WO2024133551A1 (en) | 2022-12-21 | 2024-06-27 | Syngenta Crop Protection Ag | Pesticidally active pyridazine compounds |
Family Cites Families (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3497529A (en) * | 1967-03-23 | 1970-02-24 | Sandoz Ag | Benzamides |
| PT77219B (fr) * | 1982-08-24 | 1986-02-04 | May & Baker Ltd | Procede de preparation des derives de la benzamide |
| DE4035961A1 (de) | 1990-11-02 | 1992-05-07 | Thomae Gmbh Dr K | Cyclische iminoderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| CA2057324A1 (en) | 1990-12-18 | 1992-06-19 | Lora Louise Fitch | Benzamide and sulfonamide hypoglycemic agents |
| DE4127404A1 (de) | 1991-08-19 | 1993-02-25 | Thomae Gmbh Dr K | Cyclische iminoderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| DE4236045A1 (de) | 1992-04-03 | 1993-11-04 | Teves Gmbh Alfred | Hydraulisches umschaltventil fuer eine fahrzeugbremsanlage |
| NO922913L (no) | 1992-07-22 | 1994-07-22 | Iver Hansen | Hurtigpiggede dekk |
| JPH08505391A (ja) | 1992-12-30 | 1996-06-11 | スミスクライン・ビーチャム・コーポレイション | 化合物 |
| JP2861743B2 (ja) * | 1993-07-16 | 1999-02-24 | 住友電装株式会社 | コネクタ端子のジョイント構造 |
| NZ277556A (en) | 1993-12-27 | 1997-06-24 | Eisai Co Ltd | N-phenyl(alkyl)- and n-pyridyl(alkyl)anthranilic acid derivatives; intermediates |
| US5436229A (en) | 1994-03-04 | 1995-07-25 | Eli Lilly And Company | Bisulfite adducts of arginine aldehydes |
| US5447819A (en) | 1994-05-27 | 1995-09-05 | Eastman Kodak Company | Photographic element containing high dye-yield couplers having improved reactivity |
| US5670504A (en) | 1995-02-23 | 1997-09-23 | Merck & Co. Inc. | 2,6-diaryl pyridazinones with immunosuppressant activity |
| US5638980A (en) * | 1995-09-29 | 1997-06-17 | Parks; Joseph R. | Fluid storage safety device |
| US6083986A (en) | 1996-07-26 | 2000-07-04 | Icagen, Inc. | Potassium channel inhibitors |
| US5935945A (en) | 1996-10-31 | 1999-08-10 | Merck & Co., Inc. | Methods of treating or preventing cardiac arrhythmia |
| US5969017A (en) | 1996-10-31 | 1999-10-19 | Merck & Co., Inc. | Methods of treating or preventing cardiac arrhythmia |
| TW523506B (en) | 1996-12-18 | 2003-03-11 | Ono Pharmaceutical Co | Sulfonamide or carbamide derivatives and drugs containing the same as active ingredients |
| US6407116B1 (en) | 1997-09-16 | 2002-06-18 | Takeda Chemical Industries, Inc. | Nitrogenous fused-ring compounds, process for the preparation of the same, and drugs |
| CA2315070A1 (en) | 1997-12-17 | 1999-07-01 | Schering Aktiengesellschaft | Ortho-anthranilamide derivatives as anti-coagulants |
| US6140351A (en) | 1997-12-19 | 2000-10-31 | Berlex Laboratories, Inc. | Ortho-anthranilamide derivatives as anti-coagulants |
| US6333337B1 (en) | 1998-01-27 | 2001-12-25 | Icagen, Inc. | Potassium channel inhibitors |
| CA2334258A1 (en) | 1998-06-05 | 1999-12-09 | Icagen, Inc. | Potassium channel inhibitors |
| DE19837211A1 (de) | 1998-08-17 | 2000-02-24 | Basf Ag | Verfahren zur Herstellung von Alkindiolen |
| CA2341678C (en) | 1998-09-01 | 2009-10-13 | Bristol-Myers Squibb Company | Potassium channel inhibitors and method |
| WO2000069465A1 (fr) | 1999-05-12 | 2000-11-23 | Ono Pharmaceutical Co., Ltd. | Agents anticancereux contenant des antagonistes de ep1 en tant que principe actif |
| AU5041300A (en) | 1999-05-24 | 2000-12-12 | Cor Therapeutics, Inc. | Inhibitors of factor xa |
| CA2374646A1 (en) | 1999-05-24 | 2000-11-30 | Cor Therapeutics, Inc. | Inhibitors of factor xa |
| AU5881000A (en) * | 1999-06-24 | 2001-01-09 | Smithkline Beecham Corporation | Macrophage scavenger receptor antagonists |
| DE19929076A1 (de) | 1999-06-25 | 2000-12-28 | Aventis Pharma Gmbh | Indanylsubstituierte Benzolcarbonamide, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament sowie sie enthaltende pharmazeutische Zubereitungen |
| DE19943635A1 (de) | 1999-09-13 | 2001-03-15 | Bayer Ag | Neuartige Aminodicarbonsäurederivate mit pharmazeutischen Eigenschaften |
| US6360221B1 (en) * | 1999-09-21 | 2002-03-19 | Neostar, Inc. | Method and apparatus for the production, delivery, and receipt of enhanced e-mail |
| DE19947457A1 (de) | 1999-10-02 | 2001-04-05 | Aventis Pharma Gmbh | 2'-Substituierte 1,1'-Biphenyl-2-carbonamide, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament sowie enthaltende pharmazeutische Zubereitungen |
| FR2800074B1 (fr) | 1999-10-22 | 2001-12-21 | Aventis Pharma Sa | Nouveaux oligosaccharides, leur preparation et les compositions pharmaceutiques les contenant |
| AU1917301A (en) | 1999-11-18 | 2001-05-30 | Centaur Pharmaceuticals, Inc. | Aryl nitrone therapeutics and methods for treating inflammatory bowel disease |
| DE10027151A1 (de) | 2000-05-31 | 2001-12-06 | Bayer Ag | Herbizide Mittel auf Basis von substituierten Carbonsäureamiden |
| US20020127605A1 (en) | 2000-11-28 | 2002-09-12 | Hamilton Gregory S. | Bisubstituted carbocyclic cyclophilin binding compounds and their use |
| US6498184B2 (en) | 2000-12-05 | 2002-12-24 | Akzo Nobel N.V. | Serotonergic compound for a method of treatment of hot flushes in post-menopausal women |
| WO2002050008A2 (en) | 2000-12-20 | 2002-06-27 | Warner-Lambert Company Llc | Non-halogenated phenoxy and/or benzyloxy phenols and antimicrobial compositions containing them |
| WO2002072145A1 (fr) | 2001-03-14 | 2002-09-19 | Ono Pharmaceutical Co., Ltd. | Remedes antidepresseurs contenant un antagoniste ep1 en tant que principe actif |
-
2001
- 2001-04-28 DE DE10121003A patent/DE10121003A1/de not_active Withdrawn
-
2002
- 2002-04-13 HU HU0304043A patent/HUP0304043A3/hu unknown
- 2002-04-13 WO PCT/EP2002/004138 patent/WO2002088073A1/de active IP Right Grant
- 2002-04-13 AU AU2002338494A patent/AU2002338494B2/en not_active Ceased
- 2002-04-13 AT AT02742898T patent/ATE528288T1/de active
- 2002-04-13 RS YUP-820/03A patent/RS82003A/sr unknown
- 2002-04-13 RU RU2003134544/04A patent/RU2283833C2/ru not_active IP Right Cessation
- 2002-04-13 CA CA2445341A patent/CA2445341C/en not_active Expired - Fee Related
- 2002-04-13 BR BR0209185-2A patent/BR0209185A/pt not_active IP Right Cessation
- 2002-04-13 KR KR1020037014122A patent/KR100865250B1/ko not_active IP Right Cessation
- 2002-04-13 CN CNB028082737A patent/CN100522937C/zh not_active Expired - Fee Related
- 2002-04-13 NZ NZ529129A patent/NZ529129A/en unknown
- 2002-04-13 IL IL15850402A patent/IL158504A0/xx unknown
- 2002-04-13 SK SK1326-2003A patent/SK13262003A3/sk unknown
- 2002-04-13 PL PL02363433A patent/PL363433A1/xx not_active IP Right Cessation
- 2002-04-13 MX MXPA03008419A patent/MXPA03008419A/es active IP Right Grant
- 2002-04-13 OA OA1200300278A patent/OA12598A/fr unknown
- 2002-04-13 EE EEP200300529A patent/EE05267B1/xx not_active IP Right Cessation
- 2002-04-13 UA UA20031110763A patent/UA76986C2/uk unknown
- 2002-04-13 EP EP02742898A patent/EP1385820B1/de not_active Expired - Lifetime
- 2002-04-13 CZ CZ20032921A patent/CZ20032921A3/cs unknown
- 2002-04-13 JP JP2002585377A patent/JP4231295B2/ja not_active Expired - Fee Related
- 2002-04-25 AR ARP020101502A patent/AR033623A1/es unknown
- 2002-04-25 TW TW091108496A patent/TWI259833B/zh not_active IP Right Cessation
- 2002-04-26 PE PE2002000354A patent/PE20021088A1/es not_active Application Discontinuation
- 2002-04-26 US US10/132,163 patent/US7235690B2/en not_active Expired - Lifetime
- 2002-04-26 MY MYPI20021528A patent/MY143521A/en unknown
-
2003
- 2003-03-26 EC EC2003004780A patent/ECSP034780A/es unknown
- 2003-07-08 TN TNPCT/EP2002/004138A patent/TNSN03084A1/en unknown
- 2003-09-08 ZA ZA200306991A patent/ZA200306991B/en unknown
- 2003-09-16 MA MA27313A patent/MA27002A1/fr unknown
- 2003-09-30 BG BG108215A patent/BG108215A/bg unknown
- 2003-10-07 CR CR7099A patent/CR7099A/es unknown
- 2003-10-20 IL IL158504A patent/IL158504A/en not_active IP Right Cessation
- 2003-10-23 NO NO20034751A patent/NO328872B1/no not_active IP Right Cessation
- 2003-10-27 HR HR20030871A patent/HRP20030871A2/xx not_active Application Discontinuation
-
2004
- 2004-09-23 HK HK04107327.5A patent/HK1064663A1/xx not_active IP Right Cessation
-
2006
- 2006-11-09 US US11/558,132 patent/US7332608B2/en not_active Expired - Lifetime
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ZA200306991B (en) | Anthranilic acid amides, method for the production thereof, their use as antiarrhythmia agents, and pharmaceutical preparations thereof. | |
| ZA200303931B (en) | Ortho-substituted nitrogen-containing bisaryl compounds used as potassium channel inhibitors. | |
| US7235664B2 (en) | Anthranilamides with heteroarylsulfonyl side chain, process of preparation, and use | |
| AU2008286349B2 (en) | Azabiphenylaminobenzoic acid derivatives as DHODH inhibitors | |
| US20020107245A1 (en) | Method for treating fibrotic diseases or other indications IVC | |
| US20020177586A1 (en) | Method for treating fibrotic diseases or other indications ID | |
| US20030027820A1 (en) | Method for treating fibrotic diseases or other indications V | |
| SK287464B6 (sk) | Arylované amidy furán- a tiofénkarboxylových kyselín, ich použitie a farmaceutické prostriedky, ktoré ich obsahujú | |
| TW201235040A (en) | Drug therapy for preventing or treating glaucoma | |
| CA2706241C (en) | Use of sulfonyl-substituted 2-sulfonylaminobenzoic acid n-phenylamides in the treatment of pain | |
| JP2013532728A (ja) | 哺乳動物における不整脈の急性発作の終結、洞調律の回復、不整脈の再発予防及び／又は正常洞調律の維持のための医薬組成物 | |
| ZA200506328B (en) | 2-(butyl-1sylfonylamino)-N-Ä1(R)-6methoxy-pyridin-3-yl)-propylÜ-benzamid, the use thereof in the form of drug an pharmaceutical preperations containing said compound | |
| EP1816912A2 (en) | Treatment of stroke with histamine h3 inverse agonists or histamine h3 antagonists | |
| US8106099B2 (en) | Combination of phenylcarboxamides with blockers of the IKr channel and their use for the treatment of atrial arrhythmias | |
| JP4658919B2 (ja) | フェニルカルボン酸アミドおよびＩＫｒチャンネル遮断剤の組み合わせならびに心房性不整脈を処置するためのその使用 | |
| JP2004525904A (ja) | 線維性疾患又は他の適応症ｉｉｉｃの治療方法 | |
| CA2538009A1 (en) | Combination of phenylcarboxamides with beta-adrenergic receptor blockers and use thereof for the treatment of atrial arrhythmias | |
| WO2018016611A1 (ja) | 緑内障治療薬 | |
| JP2003335671A (ja) | ピラゾロン誘導体の医薬組成物としての使用 |