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 PDF

Info

Publication number: BG107371A
Authority: BG; Bulgaria
Prior art keywords: group; substituted; compound; hydrogen atom; phenyl
Prior art date: 2000-06-27

Application number

BG107371A

Other languages

Bulgarian (bg)

English (en)

Inventor

Atsuro Nakazato

Shigeyuki Chaki

Taketoshi Okubo

Shin-Ichi Ogawa

Takaaki Ishii

Original Assignee

Taisho Pharmaceutical Co., Ltd

Priority date (The priority date 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 date listed.)

2000-06-27

Filing date

2002-12-11

Publication date

2003-08-29

2002-12-11 Application filed by Taisho Pharmaceutical Co., Ltd filed Critical Taisho Pharmaceutical Co., Ltd

2003-08-29 Publication of BG107371A publication Critical patent/BG107371A/bg

Links

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
125000001424 substituent group Chemical group 0.000 claims description 10
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
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 3
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
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 223
150000001875 compounds Chemical class 0.000 description 204
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 180
239000000243 solution Substances 0.000 description 100
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 96
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 73
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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238000006243 chemical reaction Methods 0.000 description 54
235000019441 ethanol Nutrition 0.000 description 48
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 45
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 45
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
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
239000012442 inert solvent Substances 0.000 description 39
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
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 33
239000002274 desiccant Substances 0.000 description 32
239000012044 organic layer Substances 0.000 description 32
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
241000700159 Rattus Species 0.000 description 26
238000007429 general method Methods 0.000 description 25
239000011780 sodium chloride Substances 0.000 description 24
238000003786 synthesis reaction Methods 0.000 description 24
230000009467 reduction Effects 0.000 description 23
238000012360 testing method Methods 0.000 description 23
230000015572 biosynthetic process Effects 0.000 description 22
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 21
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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
229930195733 hydrocarbon Natural products 0.000 description 11
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
150000001298 alcohols Chemical class 0.000 description 10
150000002170 ethers Chemical class 0.000 description 10
239000012280 lithium aluminium hydride Substances 0.000 description 10
230000003287 optical effect Effects 0.000 description 10
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
238000005160 1H NMR spectroscopy Methods 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
230000002378 acidificating effect Effects 0.000 description 9
229910052782 aluminium Inorganic materials 0.000 description 9
150000001412 amines Chemical class 0.000 description 9
125000004432 carbon atom Chemical group C* 0.000 description 9
230000000694 effects Effects 0.000 description 9
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 9
239000007787 solid Substances 0.000 description 9
230000009182 swimming Effects 0.000 description 9
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 8
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
239000003651 drinking water Substances 0.000 description 7
235000020188 drinking water Nutrition 0.000 description 7
238000010438 heat treatment Methods 0.000 description 7
239000011976 maleic acid Substances 0.000 description 7
229940098895 maleic acid Drugs 0.000 description 7
230000007935 neutral effect Effects 0.000 description 7
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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RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 4
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AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
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239000005557 antagonist Substances 0.000 description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
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MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 4
231100000673 dose–response relationship Toxicity 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
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125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
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NVEHQWMWLZFQIE-UHFFFAOYSA-N 2-(4-fluorophenyl)-2-[1-[(2-methylpropan-2-yl)oxycarbonyl]-3,6-dihydro-2h-pyridin-4-yl]acetic acid Chemical compound C1N(C(=O)OC(C)(C)C)CCC(C(C(O)=O)C=2C=CC(F)=CC=2)=C1 NVEHQWMWLZFQIE-UHFFFAOYSA-N 0.000 description 3
QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 3
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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)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Organic Chemistry (AREA)
Epidemiology (AREA)
Engineering & Computer Science (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pain & Pain Management (AREA)
Psychiatry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

BG107371A 2000-06-27 2002-12-11 Лекарствено средство за невроза с тревожност или депресия и пиперазинови производни BG107371A (bg)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP2000192856		2000-06-27
PCT/JP2001/005524 WO2002000259A1 (en)	2000-06-27	2001-06-27	Remedial agent for anxiety neurosis or depression and piperazine derivative

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 (et)
EP (1)	EP1295608A4 (et)
JP (1)	JP5002881B2 (et)
KR (1)	KR20030013470A (et)
CN (1)	CN1438897A (et)
AU (2)	AU2001266342B2 (et)
BG (1)	BG107371A (et)
BR (1)	BR0111976A (et)
CA (1)	CA2413506A1 (et)
CZ (1)	CZ20024165A3 (et)
EA (2)	EA200500087A1 (et)
EE (1)	EE200200717A (et)
HR (1)	HRP20030056A2 (et)
HU (1)	HUP0301719A2 (et)
IL (1)	IL153706A0 (et)
MX (1)	MXPA02012707A (et)
NO (1)	NO20026122L (et)
NZ (1)	NZ523800A (et)
PL (1)	PL360286A1 (et)
SK (1)	SK18322002A3 (et)
WO (1)	WO2002000259A1 (et)
ZA (1)	ZA200210386B (et)

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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
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
JP2005504043A (ja)	2001-08-10	2005-02-10	パラチンテクノロジーズインク．	生物学的に活性な金属ペプチド類のペプチド模倣体類
US7456184B2 (en)	2003-05-01	2008-11-25	Palatin Technologies Inc.	Melanocortin receptor-specific compounds
US7354923B2 (en)	2001-08-10	2008-04-08	Palatin Technologies, Inc.	Piperazine melanocortin-specific compounds
EP1468990A4 (en) *	2001-12-21	2006-01-04	Taisho Pharmaceutical Co Ltd	PIPERAZINE DERIVATIVE
US7727990B2 (en)	2003-05-01	2010-06-01	Palatin Technologies, Inc.	Melanocortin receptor-specific piperazine and keto-piperazine compounds
US7968548B2 (en) *	2003-05-01	2011-06-28	Palatin Technologies, Inc.	Melanocortin receptor-specific piperazine compounds with diamine groups
US7727991B2 (en)	2003-05-01	2010-06-01	Palatin Technologies, Inc.	Substituted melanocortin receptor-specific single acyl piperazine compounds
US7491723B2 (en) *	2003-10-14	2009-02-17	Wyeth	Alkanol and cycloalkanol-amine derivatives and methods of their use
US7419980B2 (en) *	2003-10-14	2008-09-02	Wyeth	Fused-aryl and heteroaryl derivatives and methods of their use
US7709484B1 (en)	2004-04-19	2010-05-04	Palatin Technologies, Inc.	Substituted melanocortin receptor-specific piperazine compounds
KR20070118103A (ko) *	2005-04-04	2007-12-13	다케다 야쿠힌 고교 가부시키가이샤	우울증 또는 불안신경증의 예방 또는 치료제
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
US20080108574A1 (en) *	2006-09-27	2008-05-08	Braincells, Inc.	Melanocortin receptor mediated modulation of neurogenesis
EP2072050A1 (en) *	2007-12-21	2009-06-24	Santhera Pharmaceuticals (Schweiz) AG	Compounds with anti-emetic effect
AR078340A1 (es) *	2009-09-07	2011-11-02	Vifor Int Ag	Antagonistas de la etanodiamina-hepcidina
WO2012027495A1 (en)	2010-08-27	2012-03-01	University Of The Pacific	Piperazinylpyrimidine analogues as protein kinase inhibitors
US9018395B2 (en)	2011-01-27	2015-04-28	Université de Montréal	Pyrazolopyridine and pyrazolopyrimidine derivatives as melanocortin-4 receptor modulators

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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
EP1085869A4 (en) *	1998-06-11	2001-10-04	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 NZ NZ523800A patent/NZ523800A/en unknown
- 2001-06-27 MX MXPA02012707A patent/MXPA02012707A/es unknown
- 2001-06-27 EP EP01943844A patent/EP1295608A4/en not_active Withdrawn
- 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 HR HR20030056A patent/HRP20030056A2/hr not_active Application Discontinuation
- 2001-06-27 AU AU2001266342A patent/AU2001266342B2/en not_active Ceased
- 2001-06-27 WO PCT/JP2001/005524 patent/WO2002000259A1/ja not_active Ceased
- 2001-06-27 PL PL36028601A patent/PL360286A1/xx not_active Application Discontinuation
- 2001-06-27 CN CN01811767A patent/CN1438897A/zh active Pending
- 2001-06-27 AU AU6634201A patent/AU6634201A/xx not_active Withdrawn
- 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 US US10/311,429 patent/US6949552B2/en not_active Expired - Fee Related
- 2001-06-27 KR KR1020027017682A patent/KR20030013470A/ko not_active Withdrawn
- 2001-06-27 EE EEP200200717A patent/EE200200717A/et unknown
- 2001-06-27 IL IL15370601A patent/IL153706A0/xx unknown
- 2001-06-27 HU HU0301719A patent/HUP0301719A2/hu unknown
- 2001-06-27 SK SK1832-2002A patent/SK18322002A3/sk unknown
- 2001-06-27 CZ CZ20024165A patent/CZ20024165A3/cs 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

Also Published As

Publication number	Publication date
PL360286A1 (en)	2004-09-06
ZA200210386B (en)	2004-02-10
HUP0301719A2 (hu)	2003-09-29
IL153706A0 (en)	2003-07-06
EA005737B1 (ru)	2005-06-30
MXPA02012707A (es)	2003-04-25
WO2002000259A1 (en)	2002-01-03
JP5002881B2 (ja)	2012-08-15
NZ523800A (en)	2005-02-25
EA200300071A1 (ru)	2003-06-26
NO20026122L (no)	2003-02-25
US6949552B2 (en)	2005-09-27
CA2413506A1 (en)	2002-12-20
SK18322002A3 (sk)	2003-09-11
AU2001266342B2 (en)	2005-01-27
NO20026122D0 (no)	2002-12-19
AU6634201A (en)	2002-01-08
EP1295608A1 (en)	2003-03-26
EP1295608A4 (en)	2004-03-31
KR20030013470A (ko)	2003-02-14
CN1438897A (zh)	2003-08-27
US20030186992A1 (en)	2003-10-02
HRP20030056A2 (en)	2005-02-28
BR0111976A (pt)	2003-12-09
CZ20024165A3 (cs)	2004-03-17
EE200200717A (et)	2004-08-16
EA200500087A1 (ru)	2005-06-30

Publication	Publication Date	Title
BG107371A (bg)	2003-08-29	Лекарствено средство за невроза с тревожност или депресия и пиперазинови производни
FI115769B (fi)	2005-07-15	Uudet piperidiiniyhdisteet, menetelmä niiden valmistamiseksi ja niitä sisältävät farmaseuttiset koostumukset
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CZ20012657A3 (cs)	2002-02-13	Piperidinové, tetrahydropyridinové a piperazinové deriváty
JP2009508963A (ja)	2009-03-05	アミド化合物および医薬組成物としてのその使用
WO2001025228A1 (en)	2001-04-12	Amine derivatives
SK15852000A3 (sk)	2001-06-11	Derivát 1-[(1-substituovaného-4-piperidinyl)metyl]-4-piperidínu, spôsob jeho prípravy, farmaceutický prípravok obsahujúci tento derivát a medziprodukt tohto derivátu
JPWO2002000259A1 (ja)	2003-09-02	不安神経症又はうつ症治療薬、及びピペラジン誘導体
SK188399A3 (en)	2000-07-11	Substituted 1,2,3,4-tetrahydronaphthalene derivatives
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JPH07133273A (ja)	1995-05-23	光学活性イミダゾリジノン誘導体とその製造方法
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US20050282816A1 (en)	2005-12-22	Pyrazinylmethyl lactam derivatives
US20050187279A1 (en)	2005-08-25	Antagonists of melanin concentrating hormone effects on the melanin concentrating hormone receptor
JP2001131149A (ja)	2001-05-15	選択的セロトニン再取り込み阻害剤
JPH037229A (ja)	1991-01-14	脳神経機能改善剤
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