CA2203878C - Certain substituted benzylamine derivatives; a new class of neuropeptide y1 specific ligands - Google Patents
Certain substituted benzylamine derivatives; a new class of neuropeptide y1 specific ligands Download PDFInfo
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- CA2203878C CA2203878C CA002203878A CA2203878A CA2203878C CA 2203878 C CA2203878 C CA 2203878C CA 002203878 A CA002203878 A CA 002203878A CA 2203878 A CA2203878 A CA 2203878A CA 2203878 C CA2203878 C CA 2203878C
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- Prior art keywords
- carbon atoms
- straight
- branched chain
- chain lower
- pharmaceutically acceptable
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- 108090000189 Neuropeptides Proteins 0.000 title abstract description 5
- 102000003797 Neuropeptides Human genes 0.000 title abstract description 5
- 150000003939 benzylamines Chemical class 0.000 title description 4
- 239000003446 ligand Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 69
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 59
- 239000001257 hydrogen Substances 0.000 claims abstract description 55
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 55
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 38
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 33
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 10
- 208000019454 Feeding and Eating disease Diseases 0.000 claims abstract description 10
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 9
- 208000032841 Bulimia Diseases 0.000 claims abstract description 7
- 206010006550 Bulimia nervosa Diseases 0.000 claims abstract description 7
- 206010020772 Hypertension Diseases 0.000 claims abstract description 7
- 208000008589 Obesity Diseases 0.000 claims abstract description 7
- 235000020824 obesity Nutrition 0.000 claims abstract description 7
- 208000030814 Eating disease Diseases 0.000 claims abstract 7
- 235000014632 disordered eating Nutrition 0.000 claims abstract 7
- 125000001424 substituent group Chemical group 0.000 claims abstract 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 73
- -1 5-pyrimidyl Chemical group 0.000 claims description 51
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 44
- 150000003839 salts Chemical class 0.000 claims description 37
- 239000008194 pharmaceutical composition Substances 0.000 claims description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 18
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical group 0.000 claims description 18
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 14
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 239000001301 oxygen Chemical group 0.000 claims description 8
- 239000011593 sulfur Substances 0.000 claims description 8
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 7
- 239000003981 vehicle Substances 0.000 claims description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
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- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
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- 125000003884 phenylalkyl group Chemical group 0.000 claims 2
- JSDCJYQGJDJRAY-UHFFFAOYSA-N 1-(2-fluorophenyl)-4-[1-(3-methoxyphenyl)cyclohexyl]piperazine Chemical compound COC1=CC=CC(C2(CCCCC2)N2CCN(CC2)C=2C(=CC=CC=2)F)=C1 JSDCJYQGJDJRAY-UHFFFAOYSA-N 0.000 claims 1
- QCOXBBPUDVIWPT-UHFFFAOYSA-N 1-(4-fluorophenyl)-4-[1-(3-methoxyphenyl)cyclohexyl]piperazine Chemical compound COC1=CC=CC(C2(CCCCC2)N2CCN(CC2)C=2C=CC(F)=CC=2)=C1 QCOXBBPUDVIWPT-UHFFFAOYSA-N 0.000 claims 1
- DGVIUBBIABVYKZ-UHFFFAOYSA-N 1-[1-(2-methoxyphenyl)cyclohexyl]-4-phenylpiperazine Chemical compound COC1=CC=CC=C1C1(N2CCN(CC2)C=2C=CC=CC=2)CCCCC1 DGVIUBBIABVYKZ-UHFFFAOYSA-N 0.000 claims 1
- KOUUGYDFGJTCKW-UHFFFAOYSA-N 1-[1-(3,5-dimethoxyphenyl)cyclohexyl]-4-phenylpiperazine Chemical compound COC1=CC(OC)=CC(C2(CCCCC2)N2CCN(CC2)C=2C=CC=CC=2)=C1 KOUUGYDFGJTCKW-UHFFFAOYSA-N 0.000 claims 1
- XOOBFSASDFGCPP-UHFFFAOYSA-N 1-[1-(3-butoxyphenyl)cyclohexyl]-4-phenylpiperazine Chemical compound CCCCOC1=CC=CC(C2(CCCCC2)N2CCN(CC2)C=2C=CC=CC=2)=C1 XOOBFSASDFGCPP-UHFFFAOYSA-N 0.000 claims 1
- LRSLWAKOKBDMEV-UHFFFAOYSA-N 1-[1-(3-ethoxyphenyl)-4-ethylcyclohexyl]-4-phenylpiperazine Chemical compound CCOC1=CC=CC(C2(CCC(CC)CC2)N2CCN(CC2)C=2C=CC=CC=2)=C1 LRSLWAKOKBDMEV-UHFFFAOYSA-N 0.000 claims 1
- JTHCCEYWYWPQDM-UHFFFAOYSA-N 1-[1-(3-ethoxyphenyl)-4-methoxycyclohexyl]-4-phenylpiperazine Chemical compound CCOC1=CC=CC(C2(CCC(CC2)OC)N2CCN(CC2)C=2C=CC=CC=2)=C1 JTHCCEYWYWPQDM-UHFFFAOYSA-N 0.000 claims 1
- HKVWLCPNTJYNBO-UHFFFAOYSA-N 1-[1-(3-ethoxyphenyl)-4-methylcyclohexyl]-4-phenylpiperazine Chemical compound CCOC1=CC=CC(C2(CCC(C)CC2)N2CCN(CC2)C=2C=CC=CC=2)=C1 HKVWLCPNTJYNBO-UHFFFAOYSA-N 0.000 claims 1
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- ISQYJTZICYKTBN-UHFFFAOYSA-N 1-[1-(3-methoxyphenyl)-3-methylcyclohexyl]-4-phenylpiperazine Chemical compound COC1=CC=CC(C2(CC(C)CCC2)N2CCN(CC2)C=2C=CC=CC=2)=C1 ISQYJTZICYKTBN-UHFFFAOYSA-N 0.000 claims 1
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- BKZCORDUSABSOK-UHFFFAOYSA-N 1-[1-(3-methoxyphenyl)cyclohexyl]-4-phenylpiperazine Chemical compound COC1=CC=CC(C2(CCCCC2)N2CCN(CC2)C=2C=CC=CC=2)=C1 BKZCORDUSABSOK-UHFFFAOYSA-N 0.000 claims 1
- UXONWHJUZYPLDN-UHFFFAOYSA-N 1-[1-(3-methoxyphenyl)cyclohexyl]-4-pyridin-2-ylpiperazine Chemical compound COC1=CC=CC(C2(CCCCC2)N2CCN(CC2)C=2N=CC=CC=2)=C1 UXONWHJUZYPLDN-UHFFFAOYSA-N 0.000 claims 1
- RSIWQIPIPPSXHS-UHFFFAOYSA-N 1-[1-(4-methoxyphenyl)cyclohexyl]-4-phenylpiperazine Chemical compound C1=CC(OC)=CC=C1C1(N2CCN(CC2)C=2C=CC=CC=2)CCCCC1 RSIWQIPIPPSXHS-UHFFFAOYSA-N 0.000 claims 1
- KKWNQYXJDARZSB-UHFFFAOYSA-N 1-[1-[3-(ethoxymethoxy)phenyl]-4-methylcyclohexyl]-4-phenylpiperazine Chemical compound CCOCOC1=CC=CC(C2(CCC(C)CC2)N2CCN(CC2)C=2C=CC=CC=2)=C1 KKWNQYXJDARZSB-UHFFFAOYSA-N 0.000 claims 1
- VPFHTAGRHOGWHD-UHFFFAOYSA-N 1-[1-[3-(methoxymethoxy)phenyl]-4-methylcyclohexyl]-4-phenylpiperazine Chemical compound COCOC1=CC=CC(C2(CCC(C)CC2)N2CCN(CC2)C=2C=CC=CC=2)=C1 VPFHTAGRHOGWHD-UHFFFAOYSA-N 0.000 claims 1
- HZWGTUBAYUCSJT-UHFFFAOYSA-N 1-[4-(3-ethoxyphenyl)oxan-4-yl]-4-phenylpiperazine Chemical compound CCOC1=CC=CC(C2(CCOCC2)N2CCN(CC2)C=2C=CC=CC=2)=C1 HZWGTUBAYUCSJT-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
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- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
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- A61P9/00—Drugs for disorders of the cardiovascular system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07D295/02—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07D295/02—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/033—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to carbocyclic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/14—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/58—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/02—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
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- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Epidemiology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Pyrane Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33547594A | 1994-11-07 | 1994-11-07 | |
| US08/335,475 | 1994-11-07 | ||
| US48497495A | 1995-06-07 | 1995-06-07 | |
| US47438395A | 1995-06-07 | 1995-06-07 | |
| US08/484,974 | 1995-06-07 | ||
| US08/474,383 | 1995-06-07 | ||
| PCT/US1995/014472 WO1996014307A1 (en) | 1994-11-07 | 1995-11-07 | Certain substituted benzylamine derivatives; a new class of neuropeptide y1 specific ligands |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2203878A1 CA2203878A1 (en) | 1996-05-17 |
| CA2203878C true CA2203878C (en) | 2002-06-25 |
Family
ID=27407057
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002203878A Expired - Fee Related CA2203878C (en) | 1994-11-07 | 1995-11-07 | Certain substituted benzylamine derivatives; a new class of neuropeptide y1 specific ligands |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JP3386814B2 (cs) |
| KR (1) | KR970707101A (cs) |
| AU (1) | AU692977B2 (cs) |
| BR (1) | BR9509610A (cs) |
| CA (1) | CA2203878C (cs) |
| CZ (1) | CZ137297A3 (cs) |
| HU (1) | HUT78089A (cs) |
| NO (1) | NO972091L (cs) |
| NZ (1) | NZ297211A (cs) |
| PL (1) | PL321136A1 (cs) |
| SK (1) | SK57097A3 (cs) |
| WO (1) | WO1996014307A1 (cs) |
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| FR2754709B1 (fr) | 1996-10-23 | 1999-03-05 | Sanofi Sa | Composition cosmetique contenant un antagoniste des recepteurs du neuropeptide gamma et alpha 2 antagonistes susceptibles d'etre incorpores dans une telle composition |
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| EP0896822B1 (en) * | 1997-08-05 | 2003-03-12 | Pfizer Products Inc. | 4-Aminopyrrole (3,2-d) pyrimidines as neuropeptide Y receptor antagonists |
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| US6187777B1 (en) | 1998-02-06 | 2001-02-13 | Amgen Inc. | Compounds and methods which modulate feeding behavior and related diseases |
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| US6531478B2 (en) | 2000-02-24 | 2003-03-11 | Cheryl P. Kordik | Amino pyrazole derivatives useful for the treatment of obesity and other disorders |
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| EP1935885A3 (en) * | 2001-05-22 | 2008-10-15 | Neurogen Corporation | Melanin concentrating hormone receptor ligands : substituted 1-benzyl-4-aryl piperazine analogues. |
| DE10213051B4 (de) * | 2002-03-23 | 2013-03-07 | Grünenthal GmbH | Substituierte 4-Aminocyclohexanole |
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| AU2009307884B2 (en) | 2008-10-22 | 2014-07-31 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| CA2741644C (en) | 2008-10-30 | 2013-05-07 | Merck Sharp & Dohme Corp. | Isonicotinamide orexin receptor antagonists |
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| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
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| BR112015002080A2 (pt) | 2012-08-02 | 2017-07-04 | Merck Sharp & Dohme | composto, composição farmacêutica, uso de um composto, e, método de tratamento ou de prevenção de um transtorno, de uma condição ou de uma doença |
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| WO2015051496A1 (en) | 2013-10-08 | 2015-04-16 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
| BR112017003745A2 (pt) | 2014-08-29 | 2017-12-05 | Tes Pharma S R L | inibidores de semialdeído descarboxilase de ácido alfa-amino-beta-carboximucônico |
| US20180134667A1 (en) | 2016-10-14 | 2018-05-17 | TES Pharma S.r.I. | Inhibitors of alpha-amino-beta-carboxymuconic acid semialdehyde decarboxylase |
| US11072602B2 (en) | 2016-12-06 | 2021-07-27 | Merck Sharp & Dohme Corp. | Antidiabetic heterocyclic compounds |
| EP3558298A4 (en) | 2016-12-20 | 2020-08-05 | Merck Sharp & Dohme Corp. | ANTIDIABETIC SPIROCHROMAN COMPOUNDS |
| SG11202104550WA (en) | 2018-11-20 | 2021-05-28 | Tes Pharma S R L | INHIBITORS OF a-AMINO-ß-CARBOXYMUCONIC ACID SEMIALDEHYDE DECARBOXYLASE |
| TW202045476A (zh) | 2019-02-13 | 2020-12-16 | 美商默沙東藥廠 | 5-烷基吡咯啶食慾素受體促效劑 |
| BR112021019465A8 (pt) | 2019-04-02 | 2022-06-07 | Aligos Therapeutics Inc | Compostos que têm como alvo prmt5 |
| US12312332B2 (en) | 2019-08-08 | 2025-05-27 | Merck Sharp & Dohme Llc | Heteroaryl pyrrolidine and piperidine orexin receptor agonists |
| MX2023001840A (es) | 2020-08-18 | 2023-03-13 | Merck Sharp & Dohme Llc | Agonistas de bicicloheptano pirrolidina de los receptores de orexina. |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4845221A (en) | 1988-04-15 | 1989-07-04 | American Home Products Corporation | Serotonergic substituted piperazinyl tetralins |
| IE65362B1 (en) * | 1989-04-22 | 1995-10-18 | Wyeth John & Brother Ltd | Piperazine derivatives |
-
1995
- 1995-11-07 KR KR1019970702989A patent/KR970707101A/ko not_active Ceased
- 1995-11-07 CA CA002203878A patent/CA2203878C/en not_active Expired - Fee Related
- 1995-11-07 CZ CZ971372A patent/CZ137297A3/cs unknown
- 1995-11-07 BR BR9509610A patent/BR9509610A/pt not_active Application Discontinuation
- 1995-11-07 HU HU9901090A patent/HUT78089A/hu unknown
- 1995-11-07 PL PL95321136A patent/PL321136A1/xx unknown
- 1995-11-07 SK SK570-97A patent/SK57097A3/sk unknown
- 1995-11-07 JP JP51549896A patent/JP3386814B2/ja not_active Expired - Fee Related
- 1995-11-07 AU AU42319/96A patent/AU692977B2/en not_active Ceased
- 1995-11-07 WO PCT/US1995/014472 patent/WO1996014307A1/en active IP Right Grant
-
1997
- 1997-04-15 NZ NZ297211A patent/NZ297211A/xx unknown
- 1997-05-06 NO NO972091A patent/NO972091L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2001520625A (ja) | 2001-10-30 |
| MX9703349A (es) | 1997-07-31 |
| AU4231996A (en) | 1996-05-31 |
| AU692977B2 (en) | 1998-06-18 |
| CZ137297A3 (cs) | 1998-04-15 |
| PL321136A1 (en) | 1997-11-24 |
| NO972091L (no) | 1997-07-02 |
| SK57097A3 (en) | 1998-10-07 |
| NO972091D0 (no) | 1997-05-06 |
| KR970707101A (ko) | 1997-12-01 |
| JP3386814B2 (ja) | 2003-03-17 |
| BR9509610A (pt) | 1997-10-28 |
| HUT78089A (hu) | 1999-08-30 |
| WO1996014307A1 (en) | 1996-05-17 |
| CA2203878A1 (en) | 1996-05-17 |
| NZ297211A (en) | 1999-01-28 |
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| EEER | Examination request | ||
| MKLA | Lapsed |