BG107371A - Лекарствено средство за невроза с тревожност или депресия и пиперазинови производни - Google Patents
Лекарствено средство за невроза с тревожност или депресия и пиперазинови производни Download PDFInfo
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- BG107371A BG107371A BG107371A BG10737102A BG107371A BG 107371 A BG107371 A BG 107371A BG 107371 A BG107371 A BG 107371A BG 10737102 A BG10737102 A BG 10737102A BG 107371 A BG107371 A BG 107371A
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- Bulgaria
- Prior art keywords
- group
- substituted
- compound
- hydrogen atom
- phenyl
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- 208000019901 Anxiety disease Diseases 0.000 title claims description 26
- 230000000246 remedial effect Effects 0.000 title abstract 2
- 208000020401 Depressive disease Diseases 0.000 title description 3
- -1 1-cyanoethyl group Chemical group 0.000 claims abstract description 101
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 44
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 32
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 31
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 18
- 125000005843 halogen group Chemical group 0.000 claims abstract description 15
- 150000004885 piperazines Chemical class 0.000 claims abstract description 11
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 10
- 239000002464 receptor antagonist Substances 0.000 claims abstract description 9
- 229940044551 receptor antagonist Drugs 0.000 claims abstract description 9
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims abstract description 7
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims abstract description 4
- 125000005493 quinolyl group Chemical group 0.000 claims abstract description 4
- 239000004480 active ingredient Substances 0.000 claims abstract 2
- 125000003277 amino group Chemical group 0.000 claims description 30
- 230000036506 anxiety Effects 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 12
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- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
- 206010029333 Neurosis Diseases 0.000 claims description 7
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 7
- 208000015238 neurotic disease Diseases 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 210000002569 neuron Anatomy 0.000 claims description 6
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 4
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- 125000000747 amidyl group Chemical group [H][N-]* 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 abstract description 27
- 125000003368 amide group Chemical group 0.000 abstract description 7
- 102000008316 Type 4 Melanocortin Receptor Human genes 0.000 abstract 1
- 108010021436 Type 4 Melanocortin Receptor Proteins 0.000 abstract 1
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- 239000000243 solution Substances 0.000 description 100
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 96
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- 230000002829 reductive effect Effects 0.000 description 70
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 66
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 44
- 238000001914 filtration Methods 0.000 description 43
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 40
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 40
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 39
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- 239000000706 filtrate Substances 0.000 description 38
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 36
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 34
- 238000000034 method Methods 0.000 description 34
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- 239000002274 desiccant Substances 0.000 description 32
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- 229920006395 saturated elastomer Polymers 0.000 description 32
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 31
- 238000002360 preparation method Methods 0.000 description 30
- 238000003756 stirring Methods 0.000 description 28
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- 238000007429 general method Methods 0.000 description 25
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- 230000015572 biosynthetic process Effects 0.000 description 22
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- 239000000203 mixture Substances 0.000 description 20
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 20
- 235000017557 sodium bicarbonate Nutrition 0.000 description 20
- 239000002253 acid Substances 0.000 description 18
- 125000006239 protecting group Chemical group 0.000 description 18
- 238000004519 manufacturing process Methods 0.000 description 17
- 230000000704 physical effect Effects 0.000 description 17
- 238000000926 separation method Methods 0.000 description 17
- 238000010898 silica gel chromatography Methods 0.000 description 17
- 239000013078 crystal Substances 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 15
- 230000009435 amidation Effects 0.000 description 15
- 238000007112 amidation reaction Methods 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- 239000003638 chemical reducing agent Substances 0.000 description 14
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 14
- 238000000605 extraction Methods 0.000 description 14
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
- 238000002474 experimental method Methods 0.000 description 12
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 11
- 239000002168 alkylating agent Substances 0.000 description 11
- 229940100198 alkylating agent Drugs 0.000 description 11
- 229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 11
- 150000008282 halocarbons Chemical class 0.000 description 11
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- 150000002430 hydrocarbons Chemical class 0.000 description 11
- 239000012312 sodium hydride Substances 0.000 description 11
- 229910000104 sodium hydride Inorganic materials 0.000 description 11
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 10
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 10
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 10
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- 230000000694 effects Effects 0.000 description 9
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- 238000001816 cooling Methods 0.000 description 8
- 150000007529 inorganic bases Chemical class 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 7
- 102400000740 Melanocyte-stimulating hormone alpha Human genes 0.000 description 7
- 101710200814 Melanotropin alpha Proteins 0.000 description 7
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 7
- 229910052796 boron Inorganic materials 0.000 description 7
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- 210000000956 olfactory bulb Anatomy 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
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- WHNFPRLDDSXQCL-UAZQEYIDSA-N α-msh Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(N)=O)NC(=O)[C@H](CO)NC(C)=O)C1=CC=C(O)C=C1 WHNFPRLDDSXQCL-UAZQEYIDSA-N 0.000 description 7
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- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 5
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- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 5
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
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- 238000009833 condensation Methods 0.000 description 5
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- 229960001367 tartaric acid Drugs 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- PHFOGMRGTJFEJF-UHFFFAOYSA-N tert-butyl 4-[1-(4-fluorophenyl)-2-[4-(4-naphthalen-1-ylbutyl)piperazin-1-yl]ethyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C(C=1C=CC(F)=CC=1)CN1CCN(CCCCC=2C3=CC=CC=C3C=CC=2)CC1 PHFOGMRGTJFEJF-UHFFFAOYSA-N 0.000 description 1
- ROUYFJUVMYHXFJ-UHFFFAOYSA-N tert-butyl 4-oxopiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(=O)CC1 ROUYFJUVMYHXFJ-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Classifications
-
- 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
- C07D295/12—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 or doubly bound nitrogen atoms
- C07D295/125—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 or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
-
- 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
- A61K31/495—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
-
- 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
- A61K31/495—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
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- 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
- C07C2601/06—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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material 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)
- Organic Chemistry (AREA)
- Epidemiology (AREA)
- Neurosurgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000192856 | 2000-06-27 | ||
| PCT/JP2001/005524 WO2002000259A1 (fr) | 2000-06-27 | 2001-06-27 | Agent therapeutique contre l'anxiete nevrotique ou la depression et derive de piperazine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BG107371A true BG107371A (bg) | 2003-08-29 |
Family
ID=18691931
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG107371A BG107371A (bg) | 2000-06-27 | 2002-12-11 | Лекарствено средство за невроза с тревожност или депресия и пиперазинови производни |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US6949552B2 (ru) |
| EP (1) | EP1295608A4 (ru) |
| JP (1) | JP5002881B2 (ru) |
| KR (1) | KR20030013470A (ru) |
| CN (1) | CN1438897A (ru) |
| AU (2) | AU2001266342B2 (ru) |
| BG (1) | BG107371A (ru) |
| BR (1) | BR0111976A (ru) |
| CA (1) | CA2413506A1 (ru) |
| CZ (1) | CZ20024165A3 (ru) |
| EA (2) | EA200500087A1 (ru) |
| EE (1) | EE200200717A (ru) |
| HR (1) | HRP20030056A2 (ru) |
| HU (1) | HUP0301719A2 (ru) |
| IL (1) | IL153706A0 (ru) |
| MX (1) | MXPA02012707A (ru) |
| NO (1) | NO20026122L (ru) |
| NZ (1) | NZ523800A (ru) |
| PL (1) | PL360286A1 (ru) |
| SK (1) | SK18322002A3 (ru) |
| WO (1) | WO2002000259A1 (ru) |
| ZA (1) | ZA200210386B (ru) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA200500087A1 (ru) | 2000-06-27 | 2005-06-30 | Тайсо Фармасьютикал Ко., Лтд. | Производные пиперазина |
| US7718802B2 (en) | 2001-08-10 | 2010-05-18 | Palatin Technologies, Inc. | Substituted melanocortin receptor-specific piperazine compounds |
| AU2002331064B2 (en) | 2001-08-10 | 2007-08-23 | Palatin Technologies, Inc. | Peptidomimetics of biologically active metallopeptides |
| US7456184B2 (en) | 2003-05-01 | 2008-11-25 | Palatin Technologies Inc. | Melanocortin receptor-specific compounds |
| US7732451B2 (en) | 2001-08-10 | 2010-06-08 | Palatin Technologies, Inc. | Naphthalene-containing melanocortin receptor-specific small molecule |
| US7655658B2 (en) | 2001-08-10 | 2010-02-02 | Palatin Technologies, Inc. | Thieno [2,3-D]pyrimidine-2,4-dione melanocortin-specific compounds |
| EP1468990A4 (en) * | 2001-12-21 | 2006-01-04 | Taisho Pharmaceutical Co Ltd | piperazine derivative |
| US7727991B2 (en) | 2003-05-01 | 2010-06-01 | Palatin Technologies, Inc. | Substituted melanocortin receptor-specific single acyl piperazine compounds |
| US7968548B2 (en) * | 2003-05-01 | 2011-06-28 | Palatin Technologies, Inc. | Melanocortin receptor-specific piperazine compounds with diamine groups |
| US7727990B2 (en) | 2003-05-01 | 2010-06-01 | Palatin Technologies, Inc. | Melanocortin receptor-specific piperazine and keto-piperazine compounds |
| US7419980B2 (en) * | 2003-10-14 | 2008-09-02 | Wyeth | Fused-aryl and heteroaryl derivatives and methods of their use |
| US7491723B2 (en) | 2003-10-14 | 2009-02-17 | Wyeth | Alkanol and cycloalkanol-amine derivatives and methods of their use |
| US7709484B1 (en) | 2004-04-19 | 2010-05-04 | Palatin Technologies, Inc. | Substituted melanocortin receptor-specific piperazine compounds |
| JP5259181B2 (ja) * | 2005-04-04 | 2013-08-07 | 武田薬品工業株式会社 | うつ病または不安神経症の予防または治療剤 |
| US20070021433A1 (en) | 2005-06-03 | 2007-01-25 | Jian-Qiang Fan | Pharmacological chaperones for treating obesity |
| US7834017B2 (en) | 2006-08-11 | 2010-11-16 | Palatin Technologies, Inc. | Diamine-containing, tetra-substituted piperazine compounds having identical 1- and 4-substituents |
| WO2008039863A2 (en) * | 2006-09-27 | 2008-04-03 | Braincells, Inc. | Composition comprising a melanocortin receptor (mcr) modulating agent alone or in combination with a second neurogenic agent for treating nervous system disorders |
| EP2072050A1 (en) * | 2007-12-21 | 2009-06-24 | Santhera Pharmaceuticals (Schweiz) AG | Compounds with anti-emetic effect |
| TW201113274A (en) | 2009-09-07 | 2011-04-16 | Vifor Int Ag | Novel ethanediamine hepcidine antagonists |
| US8609672B2 (en) | 2010-08-27 | 2013-12-17 | University Of The Pacific | Piperazinylpyrimidine analogues as protein kinase inhibitors |
| CA2825098C (en) | 2011-01-27 | 2020-03-10 | Universite De Montreal | Pyrazolopyridine and pyrazolopyrimidine derivatives as melanocortin-4 receptor modulators |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1317053A (fr) | 1961-03-17 | 1963-02-01 | Soc Ind Fab Antibiotiques Sifa | Nouveaux dérivés de la pipérazine, et procédé de préparation |
| CA918659A (en) | 1969-07-31 | 1973-01-09 | Yoshitomi Pharmaceutical Industries | 11-(4-substituted-1-piperazinyl)-dibenzo (b,f) (1,4) thiazepines |
| FR2601364B1 (fr) * | 1986-07-09 | 1988-10-21 | Adir | Nouveaux derives de la piperazine dione-2,6, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent. |
| GB9021453D0 (en) * | 1990-10-03 | 1990-11-14 | Wyeth John & Brother Ltd | Piperazine derivatives |
| JPH0641071A (ja) * | 1991-09-06 | 1994-02-15 | Taisho Pharmaceut Co Ltd | インドール酢酸エステル誘導体 |
| GB9200293D0 (en) * | 1992-01-08 | 1992-02-26 | Wyeth John & Brother Ltd | Piperazine derivatives |
| SE9700620D0 (sv) * | 1997-02-21 | 1997-02-21 | Wapharm Ab | Cykliska peptider med selektivitet för MSH-receptor subtyper |
| WO1999064002A1 (en) * | 1998-06-11 | 1999-12-16 | Merck & Co., Inc. | Spiropiperidine derivatives as melanocortin receptor agonists |
| EA200500087A1 (ru) | 2000-06-27 | 2005-06-30 | Тайсо Фармасьютикал Ко., Лтд. | Производные пиперазина |
-
2001
- 2001-06-27 EA EA200500087A patent/EA200500087A1/ru unknown
- 2001-06-27 MX MXPA02012707A patent/MXPA02012707A/es unknown
- 2001-06-27 US US10/311,429 patent/US6949552B2/en not_active Expired - Fee Related
- 2001-06-27 EP EP01943844A patent/EP1295608A4/en not_active Withdrawn
- 2001-06-27 AU AU2001266342A patent/AU2001266342B2/en not_active Ceased
- 2001-06-27 HU HU0301719A patent/HUP0301719A2/hu unknown
- 2001-06-27 PL PL36028601A patent/PL360286A1/xx not_active Application Discontinuation
- 2001-06-27 CA CA002413506A patent/CA2413506A1/en not_active Abandoned
- 2001-06-27 EA EA200300071A patent/EA005737B1/ru not_active IP Right Cessation
- 2001-06-27 KR KR1020027017682A patent/KR20030013470A/ko not_active Application Discontinuation
- 2001-06-27 EE EEP200200717A patent/EE200200717A/xx unknown
- 2001-06-27 AU AU6634201A patent/AU6634201A/xx not_active Withdrawn
- 2001-06-27 IL IL15370601A patent/IL153706A0/xx unknown
- 2001-06-27 WO PCT/JP2001/005524 patent/WO2002000259A1/ja not_active Application Discontinuation
- 2001-06-27 SK SK1832-2002A patent/SK18322002A3/sk unknown
- 2001-06-27 CZ CZ20024165A patent/CZ20024165A3/cs unknown
- 2001-06-27 CN CN01811767A patent/CN1438897A/zh active Pending
- 2001-06-27 JP JP2002505040A patent/JP5002881B2/ja not_active Expired - Fee Related
- 2001-06-27 BR BR0111976-1A patent/BR0111976A/pt not_active IP Right Cessation
- 2001-06-27 NZ NZ523800A patent/NZ523800A/en unknown
-
2002
- 2002-12-11 BG BG107371A patent/BG107371A/bg unknown
- 2002-12-19 NO NO20026122A patent/NO20026122L/no not_active Application Discontinuation
- 2002-12-20 ZA ZA200210386A patent/ZA200210386B/en unknown
-
2003
- 2003-01-27 HR HR20030056A patent/HRP20030056A2/hr not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CN1438897A (zh) | 2003-08-27 |
| HRP20030056A2 (en) | 2005-02-28 |
| EA200300071A1 (ru) | 2003-06-26 |
| EA005737B1 (ru) | 2005-06-30 |
| NZ523800A (en) | 2005-02-25 |
| AU6634201A (en) | 2002-01-08 |
| EP1295608A1 (en) | 2003-03-26 |
| CZ20024165A3 (cs) | 2004-03-17 |
| CA2413506A1 (en) | 2002-12-20 |
| KR20030013470A (ko) | 2003-02-14 |
| AU2001266342B2 (en) | 2005-01-27 |
| EE200200717A (et) | 2004-08-16 |
| WO2002000259A1 (fr) | 2002-01-03 |
| BR0111976A (pt) | 2003-12-09 |
| EP1295608A4 (en) | 2004-03-31 |
| US20030186992A1 (en) | 2003-10-02 |
| SK18322002A3 (sk) | 2003-09-11 |
| US6949552B2 (en) | 2005-09-27 |
| ZA200210386B (en) | 2004-02-10 |
| EA200500087A1 (ru) | 2005-06-30 |
| MXPA02012707A (es) | 2003-04-25 |
| HUP0301719A2 (hu) | 2003-09-29 |
| NO20026122D0 (no) | 2002-12-19 |
| NO20026122L (no) | 2003-02-25 |
| PL360286A1 (en) | 2004-09-06 |
| IL153706A0 (en) | 2003-07-06 |
| JP5002881B2 (ja) | 2012-08-15 |
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