NO310409B1 - Bisykliske amidderivater, fremstilling og anvendelse derav - Google Patents
Bisykliske amidderivater, fremstilling og anvendelse derav Download PDFInfo
- Publication number
- NO310409B1 NO310409B1 NO19954519A NO954519A NO310409B1 NO 310409 B1 NO310409 B1 NO 310409B1 NO 19954519 A NO19954519 A NO 19954519A NO 954519 A NO954519 A NO 954519A NO 310409 B1 NO310409 B1 NO 310409B1
- Authority
- NO
- Norway
- Prior art keywords
- indanylidene
- fluoro
- acetamide
- hydroxy
- difluoro
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 127
- -1 Bicyclic amide Chemical class 0.000 title description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 144
- 150000003839 salts Chemical class 0.000 claims abstract description 39
- 239000012453 solvate Substances 0.000 claims abstract description 29
- 239000003814 drug Substances 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 23
- IGSMACKWAAMMSO-VMPITWQZSA-N (2e)-2-(6-fluoro-2,3-dihydroinden-1-ylidene)acetamide Chemical compound C1=C(F)C=C2C(=C/C(=O)N)/CCC2=C1 IGSMACKWAAMMSO-VMPITWQZSA-N 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 239000011737 fluorine Substances 0.000 claims description 12
- 230000004968 inflammatory condition Effects 0.000 claims description 12
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- FAKUFORBLIQQCW-YWEYNIOJSA-N (2z)-2-(4,6-difluoro-2-hydroxy-2,3-dihydroinden-1-ylidene)acetamide Chemical compound C1=C(F)C=C(F)C2=C1C(=C/C(=O)N)/C(O)C2 FAKUFORBLIQQCW-YWEYNIOJSA-N 0.000 claims description 7
- SRIUKAFRFQIXDS-UITAMQMPSA-N (2z)-2-(6-fluoro-2-hydroxy-2,3-dihydroinden-1-ylidene)acetamide Chemical compound C1=C(F)C=C2C(=C/C(=O)N)/C(O)CC2=C1 SRIUKAFRFQIXDS-UITAMQMPSA-N 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- AQTRJSKRZHDGEX-ZZXKWVIFSA-N (2e)-2-(4,6-difluoro-2,3-dihydroinden-1-ylidene)acetamide Chemical compound C1=C(F)C=C(F)C2=C1C(=C/C(=O)N)/CC2 AQTRJSKRZHDGEX-ZZXKWVIFSA-N 0.000 claims description 6
- QGUVXUMGQJMJJB-VMPITWQZSA-N (2e)-2-(6-fluoro-3,3-dimethyl-2h-inden-1-ylidene)acetamide Chemical compound FC1=CC=C2C(C)(C)C\C(=C/C(N)=O)C2=C1 QGUVXUMGQJMJJB-VMPITWQZSA-N 0.000 claims description 6
- UHKMCBIGQTVGBL-GQCTYLIASA-N (2e)-2-(6-fluoro-3-hydroxy-2,3-dihydroinden-1-ylidene)acetamide Chemical compound C1=C(F)C=C2C(=C/C(=O)N)/CC(O)C2=C1 UHKMCBIGQTVGBL-GQCTYLIASA-N 0.000 claims description 6
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- 230000036506 anxiety Effects 0.000 claims description 6
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- 208000007101 Muscle Cramp Diseases 0.000 claims description 5
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- PBHLHXUXMLXLOX-VMPITWQZSA-N (2e)-2-(6-fluoro-3-methyl-2,3-dihydroinden-1-ylidene)acetamide Chemical compound FC1=CC=C2C(C)C\C(=C/C(N)=O)C2=C1 PBHLHXUXMLXLOX-VMPITWQZSA-N 0.000 claims description 4
- GTJPGNFDSRZYSP-VMPITWQZSA-N (2e)-n-cyclopropyl-2-(4,6-difluoro-2,3-dihydroinden-1-ylidene)acetamide Chemical compound C1CC=2C(F)=CC(F)=CC=2\C1=C\C(=O)NC1CC1 GTJPGNFDSRZYSP-VMPITWQZSA-N 0.000 claims description 4
- RAANNUXTGMASTJ-JXMROGBWSA-N (2e)-n-cyclopropyl-2-(6-fluoro-3-methyl-2,3-dihydroinden-1-ylidene)acetamide Chemical compound C12=CC(F)=CC=C2C(C)C\C1=C/C(=O)NC1CC1 RAANNUXTGMASTJ-JXMROGBWSA-N 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 4
- 229910021386 carbon form Inorganic materials 0.000 claims description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
- 201000006417 multiple sclerosis Diseases 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- HXJYZUGJRGNMCX-DHZHZOJOSA-N (2e)-2-(3-ethyl-6-fluoro-2,3-dihydroinden-1-ylidene)-n,n-dimethylacetamide Chemical compound FC1=CC=C2C(CC)C\C(=C/C(=O)N(C)C)C2=C1 HXJYZUGJRGNMCX-DHZHZOJOSA-N 0.000 claims description 2
- NXJQHWRBWAXVLU-WEVVVXLNSA-N (2e)-2-(4,6-difluoro-2,3-dihydroinden-1-ylidene)-n-propan-2-ylacetamide Chemical compound C1=C(F)C=C(F)C2=C1C(=C/C(=O)NC(C)C)/CC2 NXJQHWRBWAXVLU-WEVVVXLNSA-N 0.000 claims description 2
- NQLHEWJWIQWBFS-GORDUTHDSA-N (2e)-2-(4,6-difluoro-3-hydroxy-2,3-dihydroinden-1-ylidene)acetamide Chemical group C1=C(F)C=C(F)C2=C1C(=C/C(=O)N)/CC2O NQLHEWJWIQWBFS-GORDUTHDSA-N 0.000 claims description 2
- IBNPXNMMZBKMKL-VMPITWQZSA-N (2e)-2-(5,6-difluoro-2,3-dihydroinden-1-ylidene)-n-methylacetamide Chemical compound FC1=C(F)C=C2C(=C/C(=O)NC)/CCC2=C1 IBNPXNMMZBKMKL-VMPITWQZSA-N 0.000 claims description 2
- LAGMFMVHHNWOQK-QPJJXVBHSA-N (2e)-2-(5,6-difluoro-2,3-dihydroinden-1-ylidene)acetamide Chemical compound FC1=C(F)C=C2C(=C/C(=O)N)/CCC2=C1 LAGMFMVHHNWOQK-QPJJXVBHSA-N 0.000 claims description 2
- NMMDWTNBGZQWOW-QPJJXVBHSA-N (2e)-2-(5,7-difluoro-2,3-dihydroinden-1-ylidene)acetamide Chemical compound FC1=CC(F)=C2C(=C/C(=O)N)/CCC2=C1 NMMDWTNBGZQWOW-QPJJXVBHSA-N 0.000 claims description 2
- YUSZJFMPORWEGP-RMKNXTFCSA-N (2e)-2-(6-fluoro-3,3-dimethyl-2h-inden-1-ylidene)-n-methylacetamide Chemical compound C1=C(F)C=C2C(=C/C(=O)NC)/CC(C)(C)C2=C1 YUSZJFMPORWEGP-RMKNXTFCSA-N 0.000 claims description 2
- SBGTVGWDXBFINE-RMKNXTFCSA-N (2e)-n-cyclopropyl-2-(5,6-difluoro-2,3-dihydroinden-1-ylidene)acetamide Chemical compound C1=2C=C(F)C(F)=CC=2CC\C1=C/C(=O)NC1CC1 SBGTVGWDXBFINE-RMKNXTFCSA-N 0.000 claims description 2
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 2
- 208000009017 Athetosis Diseases 0.000 claims description 2
- 206010006811 Bursitis Diseases 0.000 claims description 2
- 206010008748 Chorea Diseases 0.000 claims description 2
- 208000001640 Fibromyalgia Diseases 0.000 claims description 2
- 201000005569 Gout Diseases 0.000 claims description 2
- 206010018634 Gouty Arthritis Diseases 0.000 claims description 2
- 208000008238 Muscle Spasticity Diseases 0.000 claims description 2
- 201000002481 Myositis Diseases 0.000 claims description 2
- 208000027089 Parkinsonian disease Diseases 0.000 claims description 2
- 206010034010 Parkinsonism Diseases 0.000 claims description 2
- 201000002661 Spondylitis Diseases 0.000 claims description 2
- 208000000491 Tendinopathy Diseases 0.000 claims description 2
- 206010043255 Tendonitis Diseases 0.000 claims description 2
- 208000004760 Tenosynovitis Diseases 0.000 claims description 2
- 206010043376 Tetanus Diseases 0.000 claims description 2
- 230000002917 arthritic effect Effects 0.000 claims description 2
- 206010008129 cerebral palsy Diseases 0.000 claims description 2
- 208000026106 cerebrovascular disease Diseases 0.000 claims description 2
- 208000012601 choreatic disease Diseases 0.000 claims description 2
- 230000002920 convulsive effect Effects 0.000 claims description 2
- 230000001660 hyperkinetic effect Effects 0.000 claims description 2
- 230000002757 inflammatory effect Effects 0.000 claims description 2
- 201000008482 osteoarthritis Diseases 0.000 claims description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
- 230000001148 spastic effect Effects 0.000 claims description 2
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- 208000005809 status epilepticus Diseases 0.000 claims description 2
- 208000011580 syndromic disease Diseases 0.000 claims description 2
- 201000004415 tendinitis Diseases 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- 125000000746 allylic group Chemical group 0.000 claims 1
- 230000002140 halogenating effect Effects 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 208000020431 spinal cord injury Diseases 0.000 claims 1
- 239000003158 myorelaxant agent Substances 0.000 abstract description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 294
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- 238000001953 recrystallisation Methods 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
- 239000004480 active ingredient Substances 0.000 description 25
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 24
- 238000000746 purification Methods 0.000 description 23
- 238000005481 NMR spectroscopy Methods 0.000 description 22
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 22
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/11—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/22—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C235/36—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/72—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms
- C07C235/76—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
- C07C235/78—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton the carbon skeleton containing rings
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/57—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and carboxyl groups, other than cyano groups, bound to the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
- C07C259/06—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms
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- C—CHEMISTRY; METALLURGY
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- 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
- C07D215/14—Radicals substituted by oxygen atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
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- 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
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
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- 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
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- 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
-
- 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
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Anesthesiology (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyrane Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB939309621A GB9309621D0 (en) | 1993-05-11 | 1993-05-11 | Amide derivatives and their therapeutic use |
PCT/GB1994/001003 WO1994026693A1 (en) | 1993-05-11 | 1994-05-10 | Bicyclic amide derivatives and their use as muscle relaxants |
Publications (3)
Publication Number | Publication Date |
---|---|
NO954519D0 NO954519D0 (no) | 1995-11-09 |
NO954519L NO954519L (no) | 1995-12-19 |
NO310409B1 true NO310409B1 (no) | 2001-07-02 |
Family
ID=10735231
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO19954519A NO310409B1 (no) | 1993-05-11 | 1995-11-09 | Bisykliske amidderivater, fremstilling og anvendelse derav |
Country Status (24)
Country | Link |
---|---|
US (1) | US5872118A (el) |
EP (2) | EP0699180B1 (el) |
JP (2) | JP3241734B2 (el) |
KR (1) | KR100417670B1 (el) |
CN (1) | CN1041720C (el) |
AT (2) | ATE197704T1 (el) |
AU (1) | AU6684894A (el) |
CA (2) | CA2162708C (el) |
DE (2) | DE69426327T2 (el) |
DK (1) | DK0699180T3 (el) |
ES (2) | ES2153420T3 (el) |
FI (1) | FI955430A (el) |
GB (1) | GB9309621D0 (el) |
GR (1) | GR3035180T3 (el) |
HK (1) | HK1003934A1 (el) |
HU (1) | HUT72419A (el) |
IL (1) | IL109610A0 (el) |
NO (1) | NO310409B1 (el) |
NZ (1) | NZ265677A (el) |
PT (1) | PT699180E (el) |
RU (1) | RU2143422C1 (el) |
TW (1) | TW275615B (el) |
WO (2) | WO1994026692A1 (el) |
ZA (1) | ZA943269B (el) |
Families Citing this family (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
MY113062A (en) * | 1994-05-10 | 2001-11-30 | The Wellcome Foundation Ltd | Amide derivatives and their therapeutic use |
ES2135065T3 (es) * | 1994-05-10 | 1999-10-16 | Wellcome Found | Derivados de amida y su uso terapeutico. |
US5661186A (en) * | 1995-02-24 | 1997-08-26 | Bristol-Myers Squibb Co. | Tetralinyl-and indanyl-ethylamides |
US6124284A (en) * | 1998-07-16 | 2000-09-26 | Glaxo Wellcome Inc. | Bicyclic amide derivatives and their use as muscle relaxants |
GB9907234D0 (en) * | 1999-03-29 | 1999-05-26 | Isis Innovation | Drug assay |
GB9926630D0 (en) * | 1999-11-10 | 2000-01-12 | Glaxo Group Ltd | Pharmacologically active compounds |
US20040116405A1 (en) * | 2001-02-06 | 2004-06-17 | Brian Cox | Use of bicyclic esters or amides for the treatment of diseases responsive to enhanced potassium channel activity |
US6956129B2 (en) * | 2001-02-16 | 2005-10-18 | Bayer Aktiengesellschaft | Polyhalogen-substituted cinnamic acids and cinnamic acid derivatives and a process for the preparation of polyhalogen-substituted cinnamic acids and cinnamic acid derivatives |
DE10145780B4 (de) | 2001-09-17 | 2012-10-04 | Merck Patent Gmbh | Fluorierte Cyclopenta[a]naphthaline und ihre Verwendung in Flüssigkristallmischungen und Displays |
DE10145779B4 (de) | 2001-09-17 | 2012-11-15 | Merck Patent Gmbh | Fluorierte Cyclopenta[b]naphthaline und ihre Verwendung in Flüssigkristallmischungen |
ES2531621T3 (es) | 2005-07-22 | 2015-03-18 | Mochida Pharmaceutical Co., Ltd. | Derivado de heterociclidenacetamida novedoso |
PE20081692A1 (es) | 2007-01-24 | 2008-12-18 | Mochida Pharm Co Ltd | Nuevo derivado de heterocicliden acetamida |
CN102258508A (zh) * | 2011-04-14 | 2011-11-30 | 威海迪素制药有限公司 | 芳基丙烯酸衍生物抗癫痫的用途 |
CN106631989B (zh) * | 2016-11-26 | 2019-07-16 | 威海迪素制药有限公司 | 一种盐酸多奈哌齐有关物质e的制备方法 |
US11543683B2 (en) | 2019-08-30 | 2023-01-03 | Johnson & Johnson Vision Care, Inc. | Multifocal contact lens displaying improved vision attributes |
US10935695B2 (en) | 2018-03-02 | 2021-03-02 | Johnson & Johnson Vision Care, Inc. | Polymerizable absorbers of UV and high energy visible light |
US11993037B1 (en) | 2018-03-02 | 2024-05-28 | Johnson & Johnson Vision Care, Inc. | Contact lens displaying improved vision attributes |
US11958824B2 (en) | 2019-06-28 | 2024-04-16 | Johnson & Johnson Vision Care, Inc. | Photostable mimics of macular pigment |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
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SE371190B (el) * | 1972-03-24 | 1974-11-11 | Kabi Ab | |
DE1241438B (de) * | 1963-05-02 | 1967-06-01 | Emil Frese Dipl Chem | Verfahren zur Herstellung von beta, beta-disubstituierten Acrylsaeureestern und den entsprechenden Acrylsaeuren |
NL7200059A (el) * | 1971-01-21 | 1972-07-25 | ||
EP0218373B1 (en) * | 1985-09-11 | 1990-03-07 | Beecham Group Plc | Chroman derivatives and analogues having antihypertensive activity |
GB8610911D0 (en) * | 1986-05-03 | 1986-06-11 | Beecham Group Plc | Active compounds |
JP2727183B2 (ja) * | 1987-03-04 | 1998-03-11 | 富士重工業 株式会社 | 自動変速機の変速制御装置 |
-
1993
- 1993-05-11 GB GB939309621A patent/GB9309621D0/en active Pending
-
1994
- 1994-05-10 US US08/549,686 patent/US5872118A/en not_active Expired - Lifetime
- 1994-05-10 ES ES94914500T patent/ES2153420T3/es not_active Expired - Lifetime
- 1994-05-10 JP JP52514194A patent/JP3241734B2/ja not_active Expired - Fee Related
- 1994-05-10 ES ES99204317T patent/ES2182454T3/es not_active Expired - Lifetime
- 1994-05-10 CA CA002162708A patent/CA2162708C/en not_active Expired - Fee Related
- 1994-05-10 CA CA002355987A patent/CA2355987C/en not_active Expired - Fee Related
- 1994-05-10 AU AU66848/94A patent/AU6684894A/en not_active Abandoned
- 1994-05-10 WO PCT/GB1994/001002 patent/WO1994026692A1/en active Application Filing
- 1994-05-10 DK DK94914500T patent/DK0699180T3/da active
- 1994-05-10 CN CN94192558A patent/CN1041720C/zh not_active Expired - Fee Related
- 1994-05-10 KR KR1019950705013A patent/KR100417670B1/ko not_active IP Right Cessation
- 1994-05-10 AT AT94914500T patent/ATE197704T1/de not_active IP Right Cessation
- 1994-05-10 NZ NZ265677A patent/NZ265677A/en unknown
- 1994-05-10 DE DE69426327T patent/DE69426327T2/de not_active Expired - Lifetime
- 1994-05-10 HU HU9501882A patent/HUT72419A/hu unknown
- 1994-05-10 WO PCT/GB1994/001003 patent/WO1994026693A1/en active IP Right Grant
- 1994-05-10 AT AT99204317T patent/ATE223373T1/de not_active IP Right Cessation
- 1994-05-10 DE DE69431316T patent/DE69431316T2/de not_active Expired - Lifetime
- 1994-05-10 IL IL10961094A patent/IL109610A0/xx not_active IP Right Cessation
- 1994-05-10 PT PT94914500T patent/PT699180E/pt unknown
- 1994-05-10 RU RU95122284A patent/RU2143422C1/ru not_active IP Right Cessation
- 1994-05-10 EP EP94914500A patent/EP0699180B1/en not_active Expired - Lifetime
- 1994-05-10 EP EP99204317A patent/EP0987248B1/en not_active Expired - Lifetime
- 1994-05-11 ZA ZA943269A patent/ZA943269B/xx unknown
- 1994-05-11 TW TW083104243A patent/TW275615B/zh active
-
1995
- 1995-11-09 NO NO19954519A patent/NO310409B1/no unknown
- 1995-11-10 FI FI955430A patent/FI955430A/fi not_active IP Right Cessation
-
1998
- 1998-04-15 HK HK98103107A patent/HK1003934A1/xx not_active IP Right Cessation
- 1998-07-06 JP JP19062998A patent/JP3302928B2/ja not_active Expired - Fee Related
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2000
- 2000-12-29 GR GR20000402870T patent/GR3035180T3/el not_active IP Right Cessation
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