UA75145C2 - Pyrrolidine oxadiazole and thiadiazole derivatives, pharmaceutical composition based thereon, a method for producing thereof (variants) - Google Patents

Pyrrolidine oxadiazole and thiadiazole derivatives, pharmaceutical composition based thereon, a method for producing thereof (variants) Download PDF

Info

Publication number: UA75145C2
Authority: UA; Ukraine
Prior art keywords: biphenyl; ylcarbonyl; oxadiazol; methyloxime; pyrrolidinone
Prior art date: 2001-06-18

Application number

UA20031211897A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Applied Research Systems

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.)

2001-06-18

Filing date

2002-06-14

Publication date

2006-03-15

2002-06-14 Application filed by Applied Research Systems filed Critical Applied Research Systems

2006-03-15 Publication of UA75145C2 publication Critical patent/UA75145C2/uk

Links

239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 14
NXDWUAQXIVWQRL-UHFFFAOYSA-N oxadiazole;pyrrolidine Chemical compound C1CCNC1.C1=CON=N1 NXDWUAQXIVWQRL-UHFFFAOYSA-N 0.000 title abstract description 9
150000004867 thiadiazoles Chemical class 0.000 title abstract 2
238000004519 manufacturing process Methods 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims abstract description 259
238000000034 method Methods 0.000 claims abstract description 116
-1 preterm labor Chemical compound 0.000 claims abstract description 69
101800000989 Oxytocin Proteins 0.000 claims abstract description 38
XNOPRXBHLZRZKH-UHFFFAOYSA-N Oxytocin Natural products N1C(=O)C(N)CSSCC(C(=O)N2C(CCC2)C(=O)NC(CC(C)C)C(=O)NCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C(C(C)CC)NC(=O)C1CC1=CC=C(O)C=C1 XNOPRXBHLZRZKH-UHFFFAOYSA-N 0.000 claims abstract description 38
102100031951 Oxytocin-neurophysin 1 Human genes 0.000 claims abstract description 38
229960001723 oxytocin Drugs 0.000 claims abstract description 38
XNOPRXBHLZRZKH-DSZYJQQASA-N oxytocin Chemical compound C([C@H]1C(=O)N[C@H](C(N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@H](N)C(=O)N1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)NCC(N)=O)=O)[C@@H](C)CC)C1=CC=C(O)C=C1 XNOPRXBHLZRZKH-DSZYJQQASA-N 0.000 claims abstract description 36
102000004279 Oxytocin receptors Human genes 0.000 claims abstract description 23
108090000876 Oxytocin receptors Proteins 0.000 claims abstract description 23
238000011282 treatment Methods 0.000 claims abstract description 23
208000005107 Premature Birth Diseases 0.000 claims abstract description 16
206010036590 Premature baby Diseases 0.000 claims abstract description 13
208000005171 Dysmenorrhea Diseases 0.000 claims abstract description 11
206010013935 Dysmenorrhoea Diseases 0.000 claims abstract description 11
238000002360 preparation method Methods 0.000 claims abstract description 10
230000002265 prevention Effects 0.000 claims abstract description 10
230000001404 mediated effect Effects 0.000 claims abstract description 9
WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims abstract description 9
UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical group C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 claims abstract description 4
239000004305 biphenyl Substances 0.000 claims description 379
125000001072 heteroaryl group Chemical group 0.000 claims description 49
125000003118 aryl group Chemical group 0.000 claims description 48
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 48
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 39
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 33
125000000753 cycloalkyl group Chemical group 0.000 claims description 25
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 23
229910052739 hydrogen Inorganic materials 0.000 claims description 23
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 22
150000003839 salts Chemical class 0.000 claims description 19
239000001257 hydrogen Substances 0.000 claims description 15
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
235000010290 biphenyl Nutrition 0.000 claims description 12
150000004820 halides Chemical class 0.000 claims description 12
229920006395 saturated elastomer Polymers 0.000 claims description 12
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 12
125000005842 heteroatom Chemical group 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 10
210000003754 fetus Anatomy 0.000 claims description 10
230000002028 premature Effects 0.000 claims description 10
102000005962 receptors Human genes 0.000 claims description 10
108020003175 receptors Proteins 0.000 claims description 10
125000002252 acyl group Chemical group 0.000 claims description 9
BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical group C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 8
125000003342 alkenyl group Chemical group 0.000 claims description 8
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
125000000304 alkynyl group Chemical group 0.000 claims description 8
125000003396 thiol group Chemical group [H]S* 0.000 claims description 8
125000003277 amino group Chemical group 0.000 claims description 7
230000027455 binding Effects 0.000 claims description 7
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 6
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 5
125000004442 acylamino group Chemical group 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 0.000 claims description 5
239000003085 diluting agent Substances 0.000 claims description 5
208000035475 disorder Diseases 0.000 claims description 5
229940126601 medicinal product Drugs 0.000 claims description 5
230000003042 antagnostic effect Effects 0.000 claims description 4
230000000903 blocking effect Effects 0.000 claims description 4
239000012634 fragment Substances 0.000 claims description 4
239000000546 pharmaceutical excipient Substances 0.000 claims description 4
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 3
125000005251 aryl acyl group Chemical group 0.000 claims description 3
125000005129 aryl carbonyl group Chemical group 0.000 claims description 3
125000006267 biphenyl group Chemical group 0.000 claims description 3
JUOXYWXXPHUSAI-UHFFFAOYSA-N ethylamino acetate Chemical compound CCNOC(C)=O JUOXYWXXPHUSAI-UHFFFAOYSA-N 0.000 claims description 3
125000005253 heteroarylacyl group Chemical group 0.000 claims description 3
125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims description 2
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims description 2
KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 2
150000001412 amines Chemical group 0.000 claims description 2
125000004104 aryloxy group Chemical group 0.000 claims description 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
125000005553 heteroaryloxy group Chemical group 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 claims 2
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims 1
WKJOQYHMXRVQDK-UHFFFAOYSA-N 2-(dimethylamino)acetamide Chemical compound CN(C)CC(N)=O WKJOQYHMXRVQDK-UHFFFAOYSA-N 0.000 claims 1
NIXQLMVKRBUSPF-UHFFFAOYSA-N 3-(dimethylamino)propanamide Chemical compound CN(C)CCC(N)=O NIXQLMVKRBUSPF-UHFFFAOYSA-N 0.000 claims 1
ZMDWVDOBEGZQJC-UHFFFAOYSA-N 3-piperidin-1-ylpropanamide Chemical compound NC(=O)CCN1CCCCC1 ZMDWVDOBEGZQJC-UHFFFAOYSA-N 0.000 claims 1
201000005569 Gout Diseases 0.000 claims 1
125000002877 alkyl aryl group Chemical group 0.000 claims 1
125000005213 alkyl heteroaryl group Chemical group 0.000 claims 1
125000004446 heteroarylalkyl group Chemical group 0.000 claims 1
125000004430 oxygen atom Chemical group O* 0.000 claims 1
150000003235 pyrrolidines Chemical class 0.000 abstract description 23
230000000694 effects Effects 0.000 abstract description 15
208000006399 Premature Obstetric Labor Diseases 0.000 abstract description 12
239000005557 antagonist Substances 0.000 abstract description 8
230000006806 disease prevention Effects 0.000 abstract 1
239000000543 intermediate Substances 0.000 description 134
239000000243 solution Substances 0.000 description 110
239000000203 mixture Substances 0.000 description 104
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 65
238000005481 NMR spectroscopy Methods 0.000 description 62
239000011541 reaction mixture Substances 0.000 description 60
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 56
239000007858 starting material Substances 0.000 description 56
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 55
238000006243 chemical reaction Methods 0.000 description 46
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 45
239000002904 solvent Substances 0.000 description 43
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 38
239000000047 product Substances 0.000 description 36
238000003818 flash chromatography Methods 0.000 description 34
125000001424 substituent group Chemical group 0.000 description 34
239000003921 oil Substances 0.000 description 30
229910052943 magnesium sulfate Inorganic materials 0.000 description 28
235000019341 magnesium sulphate Nutrition 0.000 description 28
239000002253 acid Substances 0.000 description 27
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
235000019439 ethyl acetate Nutrition 0.000 description 23
230000015572 biosynthetic process Effects 0.000 description 22
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
239000003795 chemical substances by application Substances 0.000 description 21
229910000029 sodium carbonate Inorganic materials 0.000 description 21
238000003786 synthesis reaction Methods 0.000 description 21
229940125782 compound 2 Drugs 0.000 description 20
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 18
239000012074 organic phase Substances 0.000 description 18
229910052700 potassium Inorganic materials 0.000 description 17
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 15
239000012043 crude product Substances 0.000 description 15
239000007787 solid Substances 0.000 description 15
238000003756 stirring Methods 0.000 description 15
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
239000003480 eluent Substances 0.000 description 14
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 14
238000012360 testing method Methods 0.000 description 14
102100033891 Arylsulfatase I Human genes 0.000 description 13
101000925544 Homo sapiens Arylsulfatase I Proteins 0.000 description 13
150000001735 carboxylic acids Chemical class 0.000 description 13
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VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 11
239000012267 brine Substances 0.000 description 11
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HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
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125000004169 (C1-C6) alkyl group Chemical group 0.000 description 9
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 9
239000007864 aqueous solution Substances 0.000 description 9
150000002825 nitriles Chemical class 0.000 description 9
238000000746 purification Methods 0.000 description 9
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
239000000725 suspension Substances 0.000 description 9
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
238000004587 chromatography analysis Methods 0.000 description 8
239000007924 injection Substances 0.000 description 8
238000002347 injection Methods 0.000 description 8
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238000005160 1H NMR spectroscopy Methods 0.000 description 7
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IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
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WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
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239000011975 tartaric acid Substances 0.000 description 1
SMZKPZXYDDZDJG-UHFFFAOYSA-N tert-butyl n-(cyanomethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCC#N SMZKPZXYDDZDJG-UHFFFAOYSA-N 0.000 description 1
HPWSTQITVJEUMH-UHFFFAOYSA-N tert-butyl n-[(2e)-2-amino-2-hydroxyiminoethyl]carbamate Chemical compound CC(C)(C)OC(=O)NC\C(N)=N\O HPWSTQITVJEUMH-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
VXKWYPOMXBVZSJ-UHFFFAOYSA-N tetramethyltin Chemical compound C[Sn](C)(C)C VXKWYPOMXBVZSJ-UHFFFAOYSA-N 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
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ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
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PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Substances COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 1
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238000007738 vacuum evaporation Methods 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/06—Antiabortive agents; Labour repressants
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Endocrinology (AREA)
Reproductive Health (AREA)
Diabetes (AREA)
Gynecology & Obstetrics (AREA)
Pregnancy & Childbirth (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

UA20031211897A 2001-06-18 2002-06-14 Pyrrolidine oxadiazole and thiadiazole derivatives, pharmaceutical composition based thereon, a method for producing thereof (variants) UA75145C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP01113632		2001-06-18
PCT/EP2002/006629 WO2002102799A2 (fr)	2001-06-18	2002-06-14	Derives de pyrrolidine oxadiazoles et thiadiazoles

Publications (1)

Publication Number	Publication Date
UA75145C2 true UA75145C2 (en)	2006-03-15

Family

ID=8177641

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA20031211897A UA75145C2 (en)	2001-06-18	2002-06-14	Pyrrolidine oxadiazole and thiadiazole derivatives, pharmaceutical composition based thereon, a method for producing thereof (variants)

Country Status (26)

Country	Link
US (2)	US7115639B2 (fr)
EP (1)	EP1444225B1 (fr)
JP (1)	JP4426284B2 (fr)
KR (1)	KR20040030678A (fr)
CN (1)	CN100564378C (fr)
AR (1)	AR036108A1 (fr)
AU (1)	AU2002319237B2 (fr)
BG (1)	BG108424A (fr)
BR (1)	BR0211030A (fr)
CA (1)	CA2449578C (fr)
CZ (1)	CZ20033475A3 (fr)
EA (1)	EA006212B1 (fr)
EE (1)	EE200400022A (fr)
ES (1)	ES2397305T3 (fr)
HR (1)	HRP20031017A2 (fr)
HU (1)	HUP0400238A2 (fr)
IL (1)	IL159219A0 (fr)
MX (1)	MXPA03011441A (fr)
MY (1)	MY128890A (fr)
NO (1)	NO20035399L (fr)
PL (1)	PL367275A1 (fr)
RS (1)	RS99503A (fr)
SK (1)	SK15552003A3 (fr)
UA (1)	UA75145C2 (fr)
WO (1)	WO2002102799A2 (fr)
ZA (1)	ZA200309402B (fr)

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2002
- 2002-06-14 KR KR10-2003-7016485A patent/KR20040030678A/ko not_active Ceased
- 2002-06-14 US US10/480,992 patent/US7115639B2/en not_active Expired - Fee Related
- 2002-06-14 EP EP02748785A patent/EP1444225B1/fr not_active Expired - Lifetime
- 2002-06-14 BR BR0211030-0A patent/BR0211030A/pt not_active IP Right Cessation
- 2002-06-14 HR HR20031017A patent/HRP20031017A2/xx not_active Application Discontinuation
- 2002-06-14 CN CNB028159446A patent/CN100564378C/zh not_active Expired - Fee Related
- 2002-06-14 EE EEP200400022A patent/EE200400022A/xx unknown
- 2002-06-14 CA CA2449578A patent/CA2449578C/fr not_active Expired - Fee Related
- 2002-06-14 PL PL02367275A patent/PL367275A1/xx not_active Application Discontinuation
- 2002-06-14 JP JP2003506272A patent/JP4426284B2/ja not_active Expired - Fee Related
- 2002-06-14 IL IL15921902A patent/IL159219A0/xx unknown
- 2002-06-14 EA EA200400049A patent/EA006212B1/ru not_active IP Right Cessation
- 2002-06-14 MX MXPA03011441A patent/MXPA03011441A/es active IP Right Grant
- 2002-06-14 SK SK1555-2003A patent/SK15552003A3/sk not_active Application Discontinuation
- 2002-06-14 CZ CZ20033475A patent/CZ20033475A3/cs unknown
- 2002-06-14 AU AU2002319237A patent/AU2002319237B2/en not_active Ceased
- 2002-06-14 HU HU0400238A patent/HUP0400238A2/hu unknown
- 2002-06-14 ES ES02748785T patent/ES2397305T3/es not_active Expired - Lifetime
- 2002-06-14 WO PCT/EP2002/006629 patent/WO2002102799A2/fr not_active Ceased
- 2002-06-14 RS YU99503A patent/RS99503A/sr unknown
- 2002-06-14 UA UA20031211897A patent/UA75145C2/uk unknown
- 2002-06-18 MY MYPI20022260A patent/MY128890A/en unknown
- 2002-06-21 AR ARP020102353A patent/AR036108A1/es unknown
2003
- 2003-12-03 ZA ZA200309402A patent/ZA200309402B/en unknown
- 2003-12-04 NO NO20035399A patent/NO20035399L/no unknown
- 2003-12-08 BG BG108424A patent/BG108424A/xx unknown
2006
- 2006-06-09 US US11/449,802 patent/US20060229343A1/en not_active Abandoned

Also Published As

Publication number	Publication date
US20060229343A1 (en)	2006-10-12
KR20040030678A (ko)	2004-04-09
JP4426284B2 (ja)	2010-03-03
NO20035399D0 (no)	2003-12-04
CN1639155A (zh)	2005-07-13
WO2002102799A3 (fr)	2003-04-03
NO20035399L (no)	2004-02-17
HRP20031017A2 (en)	2004-04-30
US20040220238A1 (en)	2004-11-04
US7115639B2 (en)	2006-10-03
EP1444225A2 (fr)	2004-08-11
EE200400022A (et)	2004-04-15
JP2004534804A (ja)	2004-11-18
BG108424A (en)	2005-03-31
BR0211030A (pt)	2004-06-22
HK1074204A1 (zh)	2005-11-04
IL159219A0 (en)	2004-06-01
CZ20033475A3 (en)	2004-05-12
AU2002319237B2 (en)	2008-01-03
CA2449578A1 (fr)	2002-12-27
SK15552003A3 (sk)	2004-05-04
EA200400049A1 (ru)	2004-08-26
EA006212B1 (ru)	2005-10-27
CA2449578C (fr)	2011-12-13
HUP0400238A2 (hu)	2004-07-28
RS99503A (sr)	2006-12-15
AR036108A1 (es)	2004-08-11
ZA200309402B (en)	2004-12-03
CN100564378C (zh)	2009-12-02
PL367275A1 (en)	2005-02-21
WO2002102799A2 (fr)	2002-12-27
ES2397305T3 (es)	2013-03-06
MXPA03011441A (es)	2004-07-01
MY128890A (en)	2007-02-28
EP1444225B1 (fr)	2012-10-10

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