ES2282495T3 - Uso de derivados de indol e indolino en el tratamiento de la obesidad o para la reduccion de consumo de alimento. - Google Patents
Uso de derivados de indol e indolino en el tratamiento de la obesidad o para la reduccion de consumo de alimento. Download PDFInfo
- Publication number
- ES2282495T3 ES2282495T3 ES02786300T ES02786300T ES2282495T3 ES 2282495 T3 ES2282495 T3 ES 2282495T3 ES 02786300 T ES02786300 T ES 02786300T ES 02786300 T ES02786300 T ES 02786300T ES 2282495 T3 ES2282495 T3 ES 2282495T3
- Authority
- ES
- Spain
- Prior art keywords
- aryl
- methoxy
- indol
- ethylamine
- dimethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 238000011282 treatment Methods 0.000 title claims abstract description 14
- 208000008589 Obesity Diseases 0.000 title claims abstract description 10
- 235000020824 obesity Nutrition 0.000 title claims abstract description 10
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title description 7
- 235000012631 food intake Nutrition 0.000 title description 6
- -1 4- methylpiperazinyl rings Chemical group 0.000 claims abstract description 85
- 150000001875 compounds Chemical class 0.000 claims abstract description 44
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
- 239000001257 hydrogen Substances 0.000 claims abstract description 18
- 125000003118 aryl group Chemical group 0.000 claims abstract description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 14
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000006639 cyclohexyl carbonyl group Chemical group 0.000 claims abstract description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 7
- 150000002825 nitriles Chemical class 0.000 claims abstract description 7
- 125000004193 piperazinyl group Chemical group 0.000 claims abstract description 7
- 125000003386 piperidinyl group Chemical group 0.000 claims abstract description 7
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract description 7
- 108091005435 5-HT6 receptors Proteins 0.000 claims abstract description 6
- 125000005129 aryl carbonyl group Chemical group 0.000 claims abstract description 6
- 125000006637 cyclobutyl carbonyl group Chemical group 0.000 claims abstract description 6
- 125000006638 cyclopentyl carbonyl group Chemical group 0.000 claims abstract description 6
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims abstract description 6
- 239000003814 drug Substances 0.000 claims abstract description 6
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims abstract description 6
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 150000002367 halogens Chemical class 0.000 claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims abstract description 4
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
- 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 claims abstract description 3
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims abstract description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 3
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims abstract description 3
- 230000002265 prevention Effects 0.000 claims abstract description 3
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
- AIJIQCBYMBZLJD-UHFFFAOYSA-N 2-[1-(benzenesulfonyl)-5-methoxyindol-3-yl]-n,n-dimethylethanamine Chemical compound C1=C(CCN(C)C)C2=CC(OC)=CC=C2N1S(=O)(=O)C1=CC=CC=C1 AIJIQCBYMBZLJD-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- FJLSZBZWFBWFHE-UHFFFAOYSA-N 1-(benzenesulfonyl)-3-[2-(dimethylamino)ethyl]indol-5-ol Chemical compound C12=CC=C(O)C=C2C(CCN(C)C)=CN1S(=O)(=O)C1=CC=CC=C1 FJLSZBZWFBWFHE-UHFFFAOYSA-N 0.000 claims description 2
- GACDVHSHGYKQKO-UHFFFAOYSA-N 1-(benzenesulfonyl)-3-[2-(dimethylamino)ethyl]indole-5-carbonitrile Chemical compound C12=CC=C(C#N)C=C2C(CCN(C)C)=CN1S(=O)(=O)C1=CC=CC=C1 GACDVHSHGYKQKO-UHFFFAOYSA-N 0.000 claims description 2
- SJYATYILICXNKJ-UHFFFAOYSA-N 1-(benzenesulfonyl)-5-methoxy-3-(2-piperazin-1-ylethyl)indole Chemical compound C12=CC(OC)=CC=C2N(S(=O)(=O)C=2C=CC=CC=2)C=C1CCN1CCNCC1 SJYATYILICXNKJ-UHFFFAOYSA-N 0.000 claims description 2
- KLDDKHIDNOHJGC-UHFFFAOYSA-N 1-(benzenesulfonyl)-5-methoxy-3-(2-pyrrolidin-1-ylethyl)indole Chemical compound C12=CC(OC)=CC=C2N(S(=O)(=O)C=2C=CC=CC=2)C=C1CCN1CCCC1 KLDDKHIDNOHJGC-UHFFFAOYSA-N 0.000 claims description 2
- KEOOUNJHBCNYGW-UHFFFAOYSA-N 2-(5-methoxy-1-naphthalen-2-ylsulfonylindol-3-yl)-n,n-dimethylethanamine Chemical compound C1=CC=CC2=CC(S(=O)(=O)N3C4=CC=C(C=C4C(CCN(C)C)=C3)OC)=CC=C21 KEOOUNJHBCNYGW-UHFFFAOYSA-N 0.000 claims description 2
- IPAXTAWQPQEGJN-UHFFFAOYSA-N 2-(5-methoxy-1-thiophen-2-ylsulfonylindol-3-yl)-n,n-dimethylethanamine Chemical compound C1=C(CCN(C)C)C2=CC(OC)=CC=C2N1S(=O)(=O)C1=CC=CS1 IPAXTAWQPQEGJN-UHFFFAOYSA-N 0.000 claims description 2
- CJTNSRUSBFDSOH-UHFFFAOYSA-N 2-[1-(2-chlorophenyl)sulfonyl-5-methoxyindol-3-yl]-n,n-dimethylethanamine Chemical compound C1=C(CCN(C)C)C2=CC(OC)=CC=C2N1S(=O)(=O)C1=CC=CC=C1Cl CJTNSRUSBFDSOH-UHFFFAOYSA-N 0.000 claims description 2
- HMVDWYPJGVKJPZ-UHFFFAOYSA-N 2-[1-(3-chlorophenyl)sulfonyl-5-methoxyindol-3-yl]-n,n-dimethylethanamine Chemical compound C1=C(CCN(C)C)C2=CC(OC)=CC=C2N1S(=O)(=O)C1=CC=CC(Cl)=C1 HMVDWYPJGVKJPZ-UHFFFAOYSA-N 0.000 claims description 2
- CGLZSUIRHPCPLB-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)sulfonyl-5-methoxyindol-3-yl]-n,n-dimethylethanamine Chemical compound C1=C(CCN(C)C)C2=CC(OC)=CC=C2N1S(=O)(=O)C1=CC=C(Cl)C=C1 CGLZSUIRHPCPLB-UHFFFAOYSA-N 0.000 claims description 2
- LWEWWHJJZIXSLB-UHFFFAOYSA-N 2-[1-(benzenesulfonyl)-5-methoxy-2,3-dihydroindol-3-yl]-n,n-dimethylethanamine Chemical compound C1C(CCN(C)C)C2=CC(OC)=CC=C2N1S(=O)(=O)C1=CC=CC=C1 LWEWWHJJZIXSLB-UHFFFAOYSA-N 0.000 claims description 2
- DNOJEKLHKJAPCC-UHFFFAOYSA-N 2-[1-(benzenesulfonyl)-5-methoxy-2-methylindol-3-yl]-n,n-dimethylethanamine Chemical compound CC1=C(CCN(C)C)C2=CC(OC)=CC=C2N1S(=O)(=O)C1=CC=CC=C1 DNOJEKLHKJAPCC-UHFFFAOYSA-N 0.000 claims description 2
- PLQFOHQKYPNKGC-UHFFFAOYSA-N 2-[1-(benzenesulfonyl)-5-phenylmethoxyindol-3-yl]-n,n-dimethylethanamine Chemical compound C1=C2C(CCN(C)C)=CN(S(=O)(=O)C=3C=CC=CC=3)C2=CC=C1OCC1=CC=CC=C1 PLQFOHQKYPNKGC-UHFFFAOYSA-N 0.000 claims description 2
- OJPTTYMYFMZMRB-UHFFFAOYSA-N 2-[5-methoxy-1-(4-methoxyphenyl)sulfonylindol-3-yl]-n,n-dimethylethanamine Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=C(OC)C=C2C(CCN(C)C)=C1 OJPTTYMYFMZMRB-UHFFFAOYSA-N 0.000 claims description 2
- NYUGRZAAEIFCKO-UHFFFAOYSA-N 2-[5-methoxy-1-(4-methylphenyl)sulfonylindol-3-yl]-n,n-dimethylethanamine Chemical compound C1=C(CCN(C)C)C2=CC(OC)=CC=C2N1S(=O)(=O)C1=CC=C(C)C=C1 NYUGRZAAEIFCKO-UHFFFAOYSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
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- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 125000006263 dimethyl aminosulfonyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])S(*)(=O)=O 0.000 claims description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 claims description 2
- KJOAWSBQNSIGLK-UHFFFAOYSA-N 2-[1-(benzenesulfonyl)-5-methoxyindol-3-yl]ethanamine Chemical compound C1=C(CCN)C2=CC(OC)=CC=C2N1S(=O)(=O)C1=CC=CC=C1 KJOAWSBQNSIGLK-UHFFFAOYSA-N 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
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- 125000002883 imidazolyl group Chemical group 0.000 description 1
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- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
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- 239000003550 marker Substances 0.000 description 1
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- 125000001624 naphthyl group Chemical group 0.000 description 1
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- 229940097496 nasal spray Drugs 0.000 description 1
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- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
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- 125000006413 ring segment Chemical group 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 230000000862 serotonergic effect Effects 0.000 description 1
- 239000003751 serotonin 6 antagonist Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- VILMUCRZVVVJCA-UHFFFAOYSA-M sodium glycolate Chemical compound [Na+].OCC([O-])=O VILMUCRZVVVJCA-UHFFFAOYSA-M 0.000 description 1
- 229940080313 sodium starch Drugs 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 229940032147 starch Drugs 0.000 description 1
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- 239000008174 sterile solution Substances 0.000 description 1
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- 239000011593 sulfur Substances 0.000 description 1
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- 239000000725 suspension Substances 0.000 description 1
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- 239000003826 tablet Substances 0.000 description 1
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- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
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- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
- A61K31/4045—Indole-alkylamines; Amides thereof, e.g. serotonin, melatonin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C07D209/16—Tryptamines
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Child & Adolescent Psychology (AREA)
- Epidemiology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Seasonings (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0103539 | 2001-10-23 | ||
| SE0103539A SE0103539D0 (sv) | 2001-10-23 | 2001-10-23 | New Use |
| US34059901P | 2001-12-14 | 2001-12-14 | |
| US340599P | 2001-12-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2282495T3 true ES2282495T3 (es) | 2007-10-16 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES02786300T Expired - Lifetime ES2282495T3 (es) | 2001-10-23 | 2002-10-22 | Uso de derivados de indol e indolino en el tratamiento de la obesidad o para la reduccion de consumo de alimento. |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP1438045B1 (enExample) |
| JP (1) | JP2005506368A (enExample) |
| AT (1) | ATE353646T1 (enExample) |
| CY (1) | CY1106566T1 (enExample) |
| DE (1) | DE60218194T2 (enExample) |
| DK (1) | DK1438045T3 (enExample) |
| ES (1) | ES2282495T3 (enExample) |
| PT (1) | PT1438045E (enExample) |
| WO (1) | WO2003035061A1 (enExample) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
| WO2005005439A1 (en) * | 2003-07-09 | 2005-01-20 | Suven Life Sciences Limited | Benzothiazino indoles |
| PL1558582T3 (pl) | 2003-07-22 | 2006-05-31 | Arena Pharm Inc | Diarylowe i aryloheteroarylowe pochodne mocznika jako modulatory receptora serotoninowego 5-HT2A użyteczne w profilaktyce i w leczeniu zaburzeń związanych z tym receptorem |
| ES2222828B1 (es) | 2003-07-30 | 2006-04-16 | Laboratorios Del Dr. Esteve, S.A. | Derivados de 1-sulfonilindoles, su preparacion y su aplicacion como medicamentos. |
| GB0321473D0 (en) | 2003-09-12 | 2003-10-15 | Glaxo Group Ltd | Novel compounds |
| GB0322510D0 (en) | 2003-09-25 | 2003-10-29 | Glaxo Group Ltd | Novel compounds |
| CA2552106C (en) * | 2004-01-02 | 2011-10-11 | Suven Life Sciences Limited | Novel indeno[2,1a]indenes and isoindol[2,1-a]indoles |
| EP2305352A1 (en) | 2004-04-02 | 2011-04-06 | Merck Sharp & Dohme Corp. | 5-alpha-reductase inhibitors for use in the treatment of men with metabolic and anthropometric disorders |
| WO2008039087A2 (en) * | 2006-09-29 | 2008-04-03 | Auckland Uniservices Limited | Indoline derivatives and uses thereof |
| EP1947085A1 (en) * | 2007-01-19 | 2008-07-23 | Laboratorios del Dr. Esteve S.A. | Substituted indole sulfonamide compounds, their preparation and use as medicaments |
| US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
| ES2559319T3 (es) | 2007-06-04 | 2016-02-11 | Synergy Pharmaceuticals Inc. | Agonistas de guanilato cliclasa útiles para el tratamiento de trastornos gastrointestinales, inflamación, cáncer y otros trastornos |
| EP2508177A1 (en) | 2007-12-12 | 2012-10-10 | Glaxo Group Limited | Combinations comprising 3-phenylsulfonyl-8-piperazinyl-1yl-quinoline |
| WO2009082268A2 (ru) | 2007-12-21 | 2009-07-02 | Alla Chem, Llc | ЛИГАНДЫ α-АДРЕНОЦЕПТОРОВ, ДОПАМИНОВЫХ, ГИСТАМИНОВЫХ, ИМИДАЗОЛИНОВЫХ И СЕРОТОНИНОВЫХ РЕЦЕПТОРОВ И ИХ ПРИМЕНЕНИЕ |
| WO2009123714A2 (en) | 2008-04-02 | 2009-10-08 | Arena Pharmaceuticals, Inc. | Processes for the preparation of pyrazole derivatives useful as modulators of the 5-ht2a serotonin receptor |
| CA2726917C (en) | 2008-06-04 | 2018-06-26 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| WO2010009319A2 (en) | 2008-07-16 | 2010-01-21 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal, inflammation, cancer and other disorders |
| WO2010062321A1 (en) | 2008-10-28 | 2010-06-03 | Arena Pharmaceuticals, Inc. | Processes useful for the preparation of 1-[3-(4-bromo-2-methyl-2h-pyrazol-3-yl)-4-methoxy-phenyl]-3-(2,4-difluoro-phenyl)-urea and crystalline forms related thereto |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| DK2681236T3 (en) | 2011-03-01 | 2018-04-16 | Synergy Pharmaceuticals Inc | PROCEDURE FOR MANUFACTURING GUANYLATE CYCLASE-C-AGONISTS |
| AU2014235209B2 (en) | 2013-03-15 | 2018-06-14 | Bausch Health Ireland Limited | Guanylate cyclase receptor agonists combined with other drugs |
| CA2905438A1 (en) | 2013-03-15 | 2014-09-25 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase and their uses |
| WO2014197720A2 (en) | 2013-06-05 | 2014-12-11 | Synergy Pharmaceuticals, Inc. | Ultra-pure agonists of guanylate cyclase c, method of making and using same |
| CN109562085A (zh) | 2015-06-12 | 2019-04-02 | 阿速万科学有限责任公司 | 用于预防和治疗rem睡眠行为障碍的二芳基和芳基杂芳基脲衍生物 |
| TW201720439A (zh) | 2015-07-15 | 2017-06-16 | Axovant Sciences Gmbh | 用於預防及治療與神經退化性疾病相關的幻覺之作為５－ｈｔ２ａ血清素受體的二芳基及芳基雜芳基脲衍生物 |
| EP4366731A4 (en) * | 2021-07-07 | 2025-04-16 | Terran Biosciences, Inc. | N,N-DIMETHYLTRYPTAMINE AND RELATED PSYCHEDELICS AND USES THEREOF |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4576959A (en) * | 1984-02-06 | 1986-03-18 | Eli Lilly And Company | 6-Substituted-4-dialkylaminotetrahydrobenz[c,d]indoles |
| EP0375133A1 (en) * | 1988-11-14 | 1990-06-27 | The Upjohn Company | Alpha-amino-indole-3-acetic acids useful as anti-diabetic, anti-obesity and anti-atherosclerotic agents |
| AU8876591A (en) * | 1990-11-02 | 1992-05-26 | Upjohn Company, The | Indole-3-methanamines useful as anti-diabetic, anti-obesity and anti-atherosclerotic agents |
| GB9820113D0 (en) * | 1998-09-15 | 1998-11-11 | Merck Sharp & Dohme | Therapeutic agents |
-
2002
- 2002-10-22 DE DE60218194T patent/DE60218194T2/de not_active Expired - Fee Related
- 2002-10-22 EP EP02786300A patent/EP1438045B1/en not_active Expired - Lifetime
- 2002-10-22 JP JP2003537628A patent/JP2005506368A/ja active Pending
- 2002-10-22 DK DK02786300T patent/DK1438045T3/da active
- 2002-10-22 ES ES02786300T patent/ES2282495T3/es not_active Expired - Lifetime
- 2002-10-22 AT AT02786300T patent/ATE353646T1/de not_active IP Right Cessation
- 2002-10-22 PT PT02786300T patent/PT1438045E/pt unknown
- 2002-10-22 WO PCT/SE2002/001929 patent/WO2003035061A1/en not_active Ceased
-
2007
- 2007-05-07 CY CY20071100610T patent/CY1106566T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ATE353646T1 (de) | 2007-03-15 |
| DK1438045T3 (da) | 2007-06-11 |
| PT1438045E (pt) | 2007-05-31 |
| DE60218194D1 (de) | 2007-03-29 |
| CY1106566T1 (el) | 2012-01-25 |
| EP1438045B1 (en) | 2007-02-14 |
| DE60218194T2 (de) | 2007-10-31 |
| WO2003035061A1 (en) | 2003-05-01 |
| JP2005506368A (ja) | 2005-03-03 |
| EP1438045A1 (en) | 2004-07-21 |
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