NO310654B1 - Nye aryl(alkyl)propylamider, fremgangsmåte ved deres fremstilling og farmasöytiske sammensetninger inneholdende dem - Google Patents
Nye aryl(alkyl)propylamider, fremgangsmåte ved deres fremstilling og farmasöytiske sammensetninger inneholdende dem Download PDFInfo
- Publication number
- NO310654B1 NO310654B1 NO19962209A NO962209A NO310654B1 NO 310654 B1 NO310654 B1 NO 310654B1 NO 19962209 A NO19962209 A NO 19962209A NO 962209 A NO962209 A NO 962209A NO 310654 B1 NO310654 B1 NO 310654B1
- Authority
- NO
- Norway
- Prior art keywords
- formula
- naphthyl
- compound
- alkyl
- methoxy
- Prior art date
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- 125000000217 alkyl group Chemical group 0.000 title claims abstract description 28
- 238000000034 method Methods 0.000 title claims description 30
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title description 57
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical class CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 title description 14
- 125000003118 aryl group Chemical group 0.000 title description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 20
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims abstract description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 10
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims abstract description 8
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 140
- 239000000203 mixture Substances 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 238000011282 treatment Methods 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 230000001193 melatoninergic effect Effects 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 238000000746 purification Methods 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 4
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 claims description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 4
- 150000003254 radicals Chemical class 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000003610 charcoal Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 238000004587 chromatography analysis Methods 0.000 claims description 3
- 238000002425 crystallisation Methods 0.000 claims description 3
- 230000008025 crystallization Effects 0.000 claims description 3
- 238000000605 extraction Methods 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- SAPCISUVPXEVPF-UHFFFAOYSA-N n-[3-(4-hydroxynaphthalen-1-yl)propyl]acetamide Chemical compound C1=CC=C2C(CCCNC(=O)C)=CC=C(O)C2=C1 SAPCISUVPXEVPF-UHFFFAOYSA-N 0.000 claims description 3
- ZEKCPRQRZCPPQD-UHFFFAOYSA-N n-[3-(4-phenylmethoxynaphthalen-1-yl)propyl]acetamide Chemical compound C12=CC=CC=C2C(CCCNC(=O)C)=CC=C1OCC1=CC=CC=C1 ZEKCPRQRZCPPQD-UHFFFAOYSA-N 0.000 claims description 3
- IFRNVVRYQBMVGV-UHFFFAOYSA-N n-[3-(7-methoxynaphthalen-1-yl)propyl]acetamide Chemical group C1=CC=C(CCCNC(C)=O)C2=CC(OC)=CC=C21 IFRNVVRYQBMVGV-UHFFFAOYSA-N 0.000 claims description 3
- 239000011347 resin Substances 0.000 claims description 3
- 229920005989 resin Polymers 0.000 claims description 3
- 238000005185 salting out Methods 0.000 claims description 3
- 239000000741 silica gel Substances 0.000 claims description 3
- 229910002027 silica gel Inorganic materials 0.000 claims description 3
- GOLNPGDVTXVSDF-UHFFFAOYSA-N 1-[3-(7-methoxynaphthalen-1-yl)propyl]-3-propylurea Chemical group C1=C(OC)C=C2C(CCCNC(=O)NCCC)=CC=CC2=C1 GOLNPGDVTXVSDF-UHFFFAOYSA-N 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- IXUBRGQEEHFTPV-UHFFFAOYSA-N n-[3-(7-methoxynaphthalen-1-yl)propyl]pentanamide Chemical group C1=C(OC)C=C2C(CCCNC(=O)CCCC)=CC=CC2=C1 IXUBRGQEEHFTPV-UHFFFAOYSA-N 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical compound C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 1
- 238000004140 cleaning Methods 0.000 claims 1
- RLPYYMYXJXMUDI-UHFFFAOYSA-N n-[3-(7-methoxynaphthalen-1-yl)propyl]cyclopropanecarboxamide Chemical group C12=CC(OC)=CC=C2C=CC=C1CCCNC(=O)C1CC1 RLPYYMYXJXMUDI-UHFFFAOYSA-N 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- -1 Arylalkyl propylamide Chemical compound 0.000 abstract description 20
- KEIFWROAQVVDBN-UHFFFAOYSA-N 1,2-dihydronaphthalene Chemical compound C1=CC=C2C=CCCC2=C1 KEIFWROAQVVDBN-UHFFFAOYSA-N 0.000 abstract 1
- 101100440695 Dictyostelium discoideum corB gene Proteins 0.000 abstract 1
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 39
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- 238000013459 approach Methods 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- 239000003153 chemical reaction reagent Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 238000012844 infrared spectroscopy analysis Methods 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 239000012074 organic phase Substances 0.000 description 14
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 13
- 238000004611 spectroscopical analysis Methods 0.000 description 13
- 239000000047 product Substances 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 9
- 230000033764 rhythmic process Effects 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- 102000001419 Melatonin receptor Human genes 0.000 description 7
- 108050009605 Melatonin receptor Proteins 0.000 description 7
- 239000008346 aqueous phase Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 150000001412 amines Chemical group 0.000 description 6
- 239000004202 carbamide Substances 0.000 description 6
- 230000027288 circadian rhythm Effects 0.000 description 6
- 238000011835 investigation Methods 0.000 description 6
- DRLFMBDRBRZALE-UHFFFAOYSA-N melatonin Chemical compound COC1=CC=C2NC=C(CCNC(C)=O)C2=C1 DRLFMBDRBRZALE-UHFFFAOYSA-N 0.000 description 6
- 229960003987 melatonin Drugs 0.000 description 6
- 239000012528 membrane Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- YJPIGAIKUZMOQA-UHFFFAOYSA-N Melatonin Natural products COC1=CC=C2N(C(C)=O)C=C(CCN)C2=C1 YJPIGAIKUZMOQA-UHFFFAOYSA-N 0.000 description 5
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 5
- 239000012346 acetyl chloride Substances 0.000 description 5
- 230000027455 binding Effects 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 230000000144 pharmacologic effect Effects 0.000 description 5
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 5
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- 208000019116 sleep disease Diseases 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- 241000287828 Gallus gallus Species 0.000 description 4
- 241001494479 Pecora Species 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000001110 calcium chloride Substances 0.000 description 4
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- 235000011148 calcium chloride Nutrition 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- OQURWGJAWSLGQG-UHFFFAOYSA-N 1-isocyanatopropane Chemical compound CCCN=C=O OQURWGJAWSLGQG-UHFFFAOYSA-N 0.000 description 3
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- MVLZUZCNZNMMOZ-UHFFFAOYSA-N 3-(7-methoxynaphthalen-1-yl)propanenitrile Chemical compound C1=CC=C(CCC#N)C2=CC(OC)=CC=C21 MVLZUZCNZNMMOZ-UHFFFAOYSA-N 0.000 description 3
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- 241000699670 Mus sp. Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 3
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- 238000004458 analytical method Methods 0.000 description 3
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- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
- FJDDSMSDZHURBJ-XSBOKVBDSA-N n-[2-(2-iodanyl-5-methoxy-1h-indol-3-yl)ethyl]acetamide Chemical compound COC1=CC=C2NC([125I])=C(CCNC(C)=O)C2=C1 FJDDSMSDZHURBJ-XSBOKVBDSA-N 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/58—Radicals substituted by nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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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
- C07C233/04—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 acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C233/05—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 acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
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- 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
- C07C233/18—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 a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
-
- 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
- C07C233/19—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 saturated carbon skeleton containing rings
-
- 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
- C07C233/20—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 a carbon atom of an acyclic unsaturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C233/60—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/04—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms
- C07C275/20—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
- C07C275/24—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
-
- 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
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- 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
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
-
- 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
-
- 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
-
- 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)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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FR9506433A FR2734816B1 (fr) | 1995-05-31 | 1995-05-31 | Nouveaux aryl (alkyl) propylamides, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Publications (3)
Publication Number | Publication Date |
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NO962209D0 NO962209D0 (no) | 1996-05-30 |
NO962209L NO962209L (no) | 1996-12-02 |
NO310654B1 true NO310654B1 (no) | 2001-08-06 |
Family
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NO19962209A NO310654B1 (no) | 1995-05-31 | 1996-05-30 | Nye aryl(alkyl)propylamider, fremgangsmåte ved deres fremstilling og farmasöytiske sammensetninger inneholdende dem |
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US (2) | US5731352A (zh) |
EP (1) | EP0745586B1 (zh) |
JP (1) | JPH093016A (zh) |
CN (1) | CN1060761C (zh) |
AT (1) | ATE190305T1 (zh) |
AU (1) | AU703948B2 (zh) |
CA (1) | CA2177773C (zh) |
DE (1) | DE69606915T2 (zh) |
DK (1) | DK0745586T3 (zh) |
ES (1) | ES2146365T3 (zh) |
FR (1) | FR2734816B1 (zh) |
GR (1) | GR3033087T3 (zh) |
NO (1) | NO310654B1 (zh) |
NZ (1) | NZ286696A (zh) |
PT (1) | PT745586E (zh) |
ZA (1) | ZA964483B (zh) |
Families Citing this family (42)
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ATE207460T1 (de) * | 1995-07-26 | 2001-11-15 | Takeda Chemical Industries Ltd | Benzocycloalken-verbindungen mit bindungsaffinität an den melatonin-rezeptor, ihre herstellung und verwendung |
GB9614347D0 (en) * | 1996-07-09 | 1996-09-04 | Smithkline Beecham Spa | Novel compounds |
FR2763335B1 (fr) * | 1997-05-16 | 2000-11-24 | Adir | Nouveaux composes heterocycliques substitues, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
DK0957080T3 (da) * | 1997-08-07 | 2006-10-23 | Fujimoto Brothers Co Ltd | Hidtil ukendte ethylaminderivater |
FR2771739B1 (fr) * | 1997-11-28 | 2001-04-20 | Adir | Nouveaux composes naphtaleniques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
FR2784375B1 (fr) * | 1998-10-12 | 2000-11-24 | Adir | Nouveaux derives cycliques a chaine cycloalkylenique, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
EP1499580B1 (en) * | 2002-04-01 | 2012-03-28 | The Governors of the University of Alberta | Compounds that stimulate glucose utilization and methods of use |
US20040097554A1 (en) * | 2002-10-30 | 2004-05-20 | Pfizer Inc | Heteroaryl-hexanoic acid amide derivatives as immonomodulatory agents |
FR2934855B1 (fr) * | 2008-08-05 | 2010-08-13 | Servier Lab | Nouveau procede de synthese de l'agomelatine |
EP2785681A1 (en) * | 2011-12-01 | 2014-10-08 | Ranbaxy Laboratories Limited | Process for the preparation of agomelatine |
ITMI20121444A1 (it) | 2012-08-27 | 2014-02-28 | Procos Spa | Processo per la produzione di agomelatine |
WO2014143659A1 (en) * | 2013-03-15 | 2014-09-18 | Araxes Pharma Llc | Irreversible covalent inhibitors of the gtpase k-ras g12c |
UY35464A (es) | 2013-03-15 | 2014-10-31 | Araxes Pharma Llc | Inhibidores covalentes de kras g12c. |
TWI659021B (zh) | 2013-10-10 | 2019-05-11 | 亞瑞克西斯製藥公司 | Kras g12c之抑制劑 |
JO3556B1 (ar) | 2014-09-18 | 2020-07-05 | Araxes Pharma Llc | علاجات مدمجة لمعالجة السرطان |
JP2017528498A (ja) | 2014-09-25 | 2017-09-28 | アラクセス ファーマ エルエルシー | Kras g12c変異体タンパク質のインヒビター |
US10011600B2 (en) | 2014-09-25 | 2018-07-03 | Araxes Pharma Llc | Methods and compositions for inhibition of Ras |
AU2016245864C1 (en) | 2015-04-10 | 2021-09-09 | Araxes Pharma Llc | Substituted quinazoline compounds and methods of use thereof |
ES2856880T3 (es) | 2015-04-15 | 2021-09-28 | Araxes Pharma Llc | Inhibidores tricíclicos condensados de KRAS y métodos de uso de los mismos |
US10144724B2 (en) | 2015-07-22 | 2018-12-04 | Araxes Pharma Llc | Substituted quinazoline compounds and methods of use thereof |
WO2017058807A1 (en) | 2015-09-28 | 2017-04-06 | Araxes Pharma Llc | Inhibitors of kras g12c mutant proteins |
EP3356339A1 (en) | 2015-09-28 | 2018-08-08 | Araxes Pharma LLC | Inhibitors of kras g12c mutant proteins |
US10858343B2 (en) | 2015-09-28 | 2020-12-08 | Araxes Pharma Llc | Inhibitors of KRAS G12C mutant proteins |
WO2017058768A1 (en) | 2015-09-28 | 2017-04-06 | Araxes Pharma Llc | Inhibitors of kras g12c mutant proteins |
EP3356359B1 (en) | 2015-09-28 | 2021-10-20 | Araxes Pharma LLC | Inhibitors of kras g12c mutant proteins |
US10975071B2 (en) | 2015-09-28 | 2021-04-13 | Araxes Pharma Llc | Inhibitors of KRAS G12C mutant proteins |
EP3356354A1 (en) | 2015-09-28 | 2018-08-08 | Araxes Pharma LLC | Inhibitors of kras g12c mutant proteins |
WO2017070256A2 (en) | 2015-10-19 | 2017-04-27 | Araxes Pharma Llc | Method for screening inhibitors of ras |
EP3377481A1 (en) | 2015-11-16 | 2018-09-26 | Araxes Pharma LLC | 2-substituted quinazoline compounds comprising a substituted heterocyclic group and methods of use thereof |
US9988357B2 (en) | 2015-12-09 | 2018-06-05 | Araxes Pharma Llc | Methods for preparation of quinazoline derivatives |
WO2017172979A1 (en) | 2016-03-30 | 2017-10-05 | Araxes Pharma Llc | Substituted quinazoline compounds and methods of use |
US10646488B2 (en) | 2016-07-13 | 2020-05-12 | Araxes Pharma Llc | Conjugates of cereblon binding compounds and G12C mutant KRAS, HRAS or NRAS protein modulating compounds and methods of use thereof |
EP3519402A1 (en) | 2016-09-29 | 2019-08-07 | Araxes Pharma LLC | Inhibitors of kras g12c mutant proteins |
US10377743B2 (en) | 2016-10-07 | 2019-08-13 | Araxes Pharma Llc | Inhibitors of RAS and methods of use thereof |
EP3573967A1 (en) | 2017-01-26 | 2019-12-04 | Araxes Pharma LLC | Fused hetero-hetero bicyclic compounds and methods of use thereof |
WO2018140514A1 (en) | 2017-01-26 | 2018-08-02 | Araxes Pharma Llc | 1-(6-(3-hydroxynaphthalen-1-yl)quinazolin-2-yl)azetidin-1-yl)prop-2-en-1-one derivatives and similar compounds as kras g12c inhibitors for the treatment of cancer |
WO2018140599A1 (en) | 2017-01-26 | 2018-08-02 | Araxes Pharma Llc | Benzothiophene and benzothiazole compounds and methods of use thereof |
WO2018140513A1 (en) | 2017-01-26 | 2018-08-02 | Araxes Pharma Llc | 1-(3-(6-(3-hydroxynaphthalen-1-yl)benzofuran-2-yl)azetidin-1yl)prop-2-en-1-one derivatives and similar compounds as kras g12c modulators for treating cancer |
EP3573954A1 (en) | 2017-01-26 | 2019-12-04 | Araxes Pharma LLC | Fused bicyclic benzoheteroaromatic compounds and methods of use thereof |
EP3630747A1 (en) | 2017-05-25 | 2020-04-08 | Araxes Pharma LLC | Quinazoline derivatives as modulators of mutant kras, hras or nras |
WO2018218071A1 (en) | 2017-05-25 | 2018-11-29 | Araxes Pharma Llc | Compounds and methods of use thereof for treatment of cancer |
AU2018271990A1 (en) | 2017-05-25 | 2019-12-12 | Araxes Pharma Llc | Covalent inhibitors of KRAS |
Family Cites Families (15)
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US2991290A (en) * | 1957-03-20 | 1961-07-04 | Us Vitamin Corp | Nu-alkylamino-alpha-hydroxy-alkanoic acid amides |
US3767659A (en) * | 1968-03-05 | 1973-10-23 | Colgate Palmolive Co | Derivatives of 3,4-dihydrobenzothieno(2,3-c)pyridine |
US3714193A (en) * | 1970-09-23 | 1973-01-30 | Colgate Palmolive Co | Derivatives of 1,2,3,4-tetrahydro-5h-benzothieno[2,3-c]azepines |
US3759895A (en) * | 1971-12-20 | 1973-09-18 | Eastman Kodak Co | Benzothiazolyl azo indole compounds |
US3829411A (en) * | 1972-03-29 | 1974-08-13 | Eastman Kodak Co | Thiadiazolyl-azo-indole compounds |
US4602035A (en) * | 1983-12-07 | 1986-07-22 | Hoechst-Roussel Pharmaceuticals Inc. | Antidepressant (3-aryl-2,3-dihydrobenzofuran-3-yl)alkylamines |
US4992464A (en) * | 1987-02-10 | 1991-02-12 | Abbott Laboratories | Heteroaryl N-hydroxy amides and ureas with polar substituents as 5-lipoxygenase inhibitors |
FR2658818B1 (fr) * | 1990-02-27 | 1993-12-31 | Adir Cie | Nouveaux derives a structure naphtalenique, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
US5095031A (en) * | 1990-08-20 | 1992-03-10 | Abbott Laboratories | Indole derivatives which inhibit leukotriene biosynthesis |
JPH04173777A (ja) * | 1990-10-31 | 1992-06-22 | Whitby Res Inc | メラトニン類似体 |
US5145845A (en) * | 1991-05-14 | 1992-09-08 | Warner-Lambert Co. | Substituted 2-carboxylindoles having pharmaceutical activity |
FR2696453B1 (fr) * | 1992-10-02 | 1994-12-23 | Adir | Nouveaux arylalkyl(thio)amides, leur procédé de préparation, et les compositions pharmaceutiques qui les contiennent. |
NZ250916A (en) * | 1993-02-27 | 1995-08-28 | Nihon Nohyaku Co Ltd | N-heteroaryl-n'-phenylureas, their use as acat inhibitors |
JP3908798B2 (ja) * | 1994-09-12 | 2007-04-25 | 武田薬品工業株式会社 | ベンゾシクロアルケン類、その製造法および剤 |
FR2734814B1 (fr) * | 1995-05-31 | 1997-07-04 | Adir | Nouveaux composes alkoxy-aryles, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
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1995
- 1995-05-31 FR FR9506433A patent/FR2734816B1/fr not_active Expired - Lifetime
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1996
- 1996-05-27 JP JP8131950A patent/JPH093016A/ja active Pending
- 1996-05-29 AU AU54561/96A patent/AU703948B2/en not_active Ceased
- 1996-05-30 ES ES96401157T patent/ES2146365T3/es not_active Expired - Lifetime
- 1996-05-30 NZ NZ286696A patent/NZ286696A/en unknown
- 1996-05-30 DE DE69606915T patent/DE69606915T2/de not_active Expired - Fee Related
- 1996-05-30 PT PT96401157T patent/PT745586E/pt unknown
- 1996-05-30 DK DK96401157T patent/DK0745586T3/da active
- 1996-05-30 CN CN96107792A patent/CN1060761C/zh not_active Expired - Fee Related
- 1996-05-30 US US08/655,635 patent/US5731352A/en not_active Expired - Fee Related
- 1996-05-30 AT AT96401157T patent/ATE190305T1/de not_active IP Right Cessation
- 1996-05-30 NO NO19962209A patent/NO310654B1/no not_active Application Discontinuation
- 1996-05-30 EP EP96401157A patent/EP0745586B1/fr not_active Expired - Lifetime
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- 1996-05-31 ZA ZA964483A patent/ZA964483B/xx unknown
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1997
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2000
- 2000-03-29 GR GR20000400776T patent/GR3033087T3/el not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
FR2734816A1 (fr) | 1996-12-06 |
DE69606915D1 (de) | 2000-04-13 |
EP0745586A1 (fr) | 1996-12-04 |
CA2177773A1 (fr) | 1996-12-01 |
EP0745586B1 (fr) | 2000-03-08 |
PT745586E (pt) | 2000-06-30 |
AU703948B2 (en) | 1999-04-01 |
US5731352A (en) | 1998-03-24 |
DK0745586T3 (da) | 2000-07-31 |
CN1145897A (zh) | 1997-03-26 |
CA2177773C (fr) | 2000-10-03 |
DE69606915T2 (de) | 2000-10-12 |
US5760071A (en) | 1998-06-02 |
ATE190305T1 (de) | 2000-03-15 |
NO962209D0 (no) | 1996-05-30 |
JPH093016A (ja) | 1997-01-07 |
CN1060761C (zh) | 2001-01-17 |
FR2734816B1 (fr) | 1997-07-04 |
ES2146365T3 (es) | 2000-08-01 |
NO962209L (no) | 1996-12-02 |
ZA964483B (en) | 1996-12-12 |
NZ286696A (en) | 1997-09-22 |
GR3033087T3 (en) | 2000-08-31 |
AU5456196A (en) | 1996-12-12 |
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