BG64530B1 - Метод за синтез на пироламиди - Google Patents

Метод за синтез на пироламиди Download PDF

Info

Publication number: BG64530B1
Authority: BG; Bulgaria
Prior art keywords: oxo; tetrahydro; methyl; carboxylic acid; phenyl
Prior art date: 1997-11-13

Application number

BG104413A

Other languages

Bulgarian (bg)

English (en)

Other versions

BG104413A (en

Inventor

John RAGAN

Teresa MAKOWSKI

Ende David Am

Pamela Clifford

Gregory Young

Alyson Conrad

Shane EISENBEIS

Douglas Allen

George Quallich

Original Assignee

Pfizer Products Inc.

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.)

1997-11-13

Filing date

2000-05-09

Publication date

2005-06-30

2000-05-09 Application filed by Pfizer Products Inc. filed Critical Pfizer Products Inc.

2001-02-28 Publication of BG104413A publication Critical patent/BG104413A/xx

2005-06-30 Publication of BG64530B1 publication Critical patent/BG64530B1/bg

Links

238000000034 method Methods 0.000 title claims abstract description 31
-1 pyrrole amides Chemical class 0.000 title claims description 23
238000003786 synthesis reaction Methods 0.000 title description 5
230000015572 biosynthetic process Effects 0.000 title description 4
KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 title description 3
238000006243 chemical reaction Methods 0.000 claims abstract description 21
239000002253 acid Substances 0.000 claims abstract description 9
150000001875 compounds Chemical class 0.000 claims description 47
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 12
230000008569 process Effects 0.000 claims description 10
YWUVOJJHVFLNJA-UHFFFAOYSA-N 2-fluoro-4-methoxyaniline Chemical compound COC1=CC=C(N)C(F)=C1 YWUVOJJHVFLNJA-UHFFFAOYSA-N 0.000 claims description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 8
PXIYUIZGOHSVAZ-UHFFFAOYSA-N 4-oxo-5,6,7,8-tetrahydrocyclohepta[b]furan-3-carboxylic acid Chemical compound C1CCCC(=O)C2=C1OC=C2C(=O)O PXIYUIZGOHSVAZ-UHFFFAOYSA-N 0.000 claims description 7
QQPMDRGNNFKVEL-UHFFFAOYSA-N 4,5,6,7-tetrahydro-1-benzofuran-3-carboxylic acid Chemical compound C1CCCC2=C1OC=C2C(=O)O QQPMDRGNNFKVEL-UHFFFAOYSA-N 0.000 claims description 6
XGNXYCFREOZBOL-UHFFFAOYSA-N 1,3-benzodioxol-5-amine Chemical compound NC1=CC=C2OCOC2=C1 XGNXYCFREOZBOL-UHFFFAOYSA-N 0.000 claims description 5
IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 claims description 5
239000012442 inert solvent Substances 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
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 claims description 4
IHCCAYCGZOLTEU-UHFFFAOYSA-N 3-furoic acid Chemical compound OC(=O)C=1C=COC=1 IHCCAYCGZOLTEU-UHFFFAOYSA-N 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
125000000623 heterocyclic group Chemical group 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 claims description 4
KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 claims description 3
MIOVLJHOMINVHH-UHFFFAOYSA-N 4-oxo-5,6-dihydrocyclopenta[b]furan-3-carboxylic acid Chemical compound C1CC(=O)C2=C1OC=C2C(=O)O MIOVLJHOMINVHH-UHFFFAOYSA-N 0.000 claims description 3
AAMWMZBIMBWXPQ-UHFFFAOYSA-N 5,6,7,8-tetrahydro-4h-cyclohepta[b]furan-3-carboxylic acid Chemical compound C1CCCCC2=C1OC=C2C(=O)O AAMWMZBIMBWXPQ-UHFFFAOYSA-N 0.000 claims description 3
LTSBKYGKJDMJNJ-UHFFFAOYSA-N 6-methyl-4-oxo-6,7-dihydro-5h-1-benzofuran-3-carboxylic acid Chemical compound O=C1CC(C)CC2=C1C(C(O)=O)=CO2 LTSBKYGKJDMJNJ-UHFFFAOYSA-N 0.000 claims description 3
150000008064 anhydrides Chemical class 0.000 claims description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
229920001774 Perfluoroether Polymers 0.000 claims description 2
239000007810 chemical reaction solvent Substances 0.000 claims description 2
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical group CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims description 2
125000005010 perfluoroalkyl group Chemical group 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
IRSZDNMUBYZIOH-UHFFFAOYSA-N tert-butyl n-[2-[4-[(4-oxo-1,5,6,7-tetrahydroindole-3-carbonyl)amino]phenyl]ethyl]carbamate Chemical compound C1=CC(CCNC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 IRSZDNMUBYZIOH-UHFFFAOYSA-N 0.000 claims 1
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RGHQKFQZGLKBCF-UHFFFAOYSA-N 2-bromoethyl acetate Chemical compound CC(=O)OCCBr RGHQKFQZGLKBCF-UHFFFAOYSA-N 0.000 abstract 1
150000004982 aromatic amines Chemical class 0.000 abstract 1
150000004820 halides Chemical class 0.000 abstract 1
238000005481 NMR spectroscopy Methods 0.000 description 39
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 28
239000000243 solution Substances 0.000 description 22
238000007429 general method Methods 0.000 description 19
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 16
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239000007787 solid Substances 0.000 description 15
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
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239000003921 oil Substances 0.000 description 10
235000019198 oils Nutrition 0.000 description 10
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
102000005962 receptors Human genes 0.000 description 8
108020003175 receptors Proteins 0.000 description 8
230000009471 action Effects 0.000 description 7
150000001557 benzodiazepines Chemical class 0.000 description 7
238000001816 cooling Methods 0.000 description 7
239000000047 product Substances 0.000 description 7
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
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239000000203 mixture Substances 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
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OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 description 4
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UIBDRXZQWRSOKA-UHFFFAOYSA-N 2-(5-aminopyridin-2-yl)oxyethanol Chemical compound NC1=CC=C(OCCO)N=C1 UIBDRXZQWRSOKA-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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229910052943 magnesium sulfate Inorganic materials 0.000 description 3
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150000001805 chlorine compounds Chemical class 0.000 description 1
208000010877 cognitive disease Diseases 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
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229960003528 flurazepam Drugs 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
239000011521 glass Substances 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
230000002102 hyperpolarization Effects 0.000 description 1
239000003326 hypnotic agent Substances 0.000 description 1
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JLKRJHPQNYVSGM-UHFFFAOYSA-N methyl-(4-nitro-benzyl)-amine Chemical compound CNCC1=CC=C([N+]([O-])=O)C=C1 JLKRJHPQNYVSGM-UHFFFAOYSA-N 0.000 description 1
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QOBQEJNQDPECSX-UHFFFAOYSA-N n-(2-fluoro-4-methoxyphenyl)-4-oxo-5,6,7,8-tetrahydrocyclohepta[b]furan-3-carboxamide Chemical compound FC1=CC(OC)=CC=C1NC(=O)C1=COC2=C1C(=O)CCCC2 QOBQEJNQDPECSX-UHFFFAOYSA-N 0.000 description 1
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BBUGZFUOHBBWKT-UHFFFAOYSA-N n-(4-fluorophenyl)-6-methyl-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C1=2C(=O)CC(C)CC=2NC=C1C(=O)NC1=CC=C(F)C=C1 BBUGZFUOHBBWKT-UHFFFAOYSA-N 0.000 description 1
210000001640 nerve ending Anatomy 0.000 description 1
210000002569 neuron Anatomy 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
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230000003389 potentiating effect Effects 0.000 description 1
230000003518 presynaptic effect Effects 0.000 description 1
XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
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230000002829 reductive effect Effects 0.000 description 1
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230000001624 sedative effect Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
210000000273 spinal nerve root Anatomy 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
210000000225 synapse Anatomy 0.000 description 1
230000005062 synaptic transmission Effects 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
JUMUBLTUERLNEA-UHFFFAOYSA-N tert-butyl n-methyl-n-[[4-[(4-oxo-1,5,6,7-tetrahydroindole-3-carbonyl)amino]phenyl]methyl]carbamate Chemical compound C1=CC(CN(C)C(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 JUMUBLTUERLNEA-UHFFFAOYSA-N 0.000 description 1
238000012360 testing method Methods 0.000 description 1
238000011287 therapeutic dose Methods 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000000844 transformation Methods 0.000 description 1
JOFWLTCLBGQGBO-UHFFFAOYSA-N triazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1Cl JOFWLTCLBGQGBO-UHFFFAOYSA-N 0.000 description 1
229960003386 triazolam Drugs 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- A61P25/24—Antidepressants
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans 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 carbon atoms of the hetero ring
- C07D307/83—Oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans 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 carbon atoms of the hetero ring
- C07D307/84—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Neurology (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Plural Heterocyclic Compounds (AREA)
Pyrrole Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Indole Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Furan Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Treatment Of Liquids With Adsorbents In General (AREA)
Tea And Coffee (AREA)
Fats And Perfumes (AREA)

BG104413A 1997-11-13 2000-05-09 Метод за синтез на пироламиди BG64530B1 (bg)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US6542297P	1997-11-13	1997-11-13
US7426698P	1998-02-10	1998-02-10

Publications (2)

Publication Number	Publication Date
BG104413A BG104413A (en)	2001-02-28
BG64530B1 true BG64530B1 (bg)	2005-06-30

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ID=26745584

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BG104413A BG64530B1 (bg)	1997-11-13	2000-05-09	Метод за синтез на пироламиди

Country Status (35)

Country	Link
US (1)	US6262272B1 (fr)
EP (1)	EP1030838B1 (fr)
JP (1)	JP3497469B2 (fr)
KR (1)	KR100386722B1 (fr)
CN (2)	CN1280566A (fr)
AT (1)	ATE231492T1 (fr)
AU (1)	AU745788B2 (fr)
BG (1)	BG64530B1 (fr)
BR (1)	BR9814161A (fr)
CA (1)	CA2310095A1 (fr)
CZ (1)	CZ20001769A3 (fr)
DE (1)	DE69810959T2 (fr)
DK (1)	DK1030838T3 (fr)
DZ (1)	DZ2651A1 (fr)
EA (1)	EA002243B1 (fr)
ES (1)	ES2186232T3 (fr)
HR (1)	HRP20000298A2 (fr)
HU (1)	HUP0100235A3 (fr)
ID (1)	ID24135A (fr)
IL (1)	IL135710A0 (fr)
IS (1)	IS5469A (fr)
MA (1)	MA24697A1 (fr)
NO (1)	NO20002214L (fr)
NZ (1)	NZ503916A (fr)
OA (1)	OA11378A (fr)
PA (1)	PA8462901A1 (fr)
PL (1)	PL340554A1 (fr)
PT (1)	PT1030838E (fr)
SK (1)	SK6872000A3 (fr)
TN (1)	TNSN98204A1 (fr)
TR (1)	TR200001343T2 (fr)
TW (1)	TW509675B (fr)
UY (1)	UY25249A1 (fr)
WO (1)	WO1999025684A1 (fr)
YU (1)	YU27300A (fr)

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IL147971A0 (en)	1999-08-31	2002-09-12	Neurogen Corp	Fused pyrrolecarboxamides: gaba brain receptor ligands
JP2004508359A (ja) *	2000-09-06	2004-03-18	ニューロゲン　コーポレイション	アリール置換テトラヒドロインダゾール、及び、ｇａｂａ−ａ受容体に対するリガンドとしてのそれらの使用
MXPA03004939A (es) *	2000-12-04	2003-09-10	Pfizer Prod Inc	Sintesis de pirrolamidas.
EP1472252A1 (fr)	2002-02-07	2004-11-03	Neurogen Corporation	Arylamides d'acide pyrazolecarboxylique substitues, fusionnes, et composes associes
US20080153629A1 (en) *	2004-05-07	2008-06-26	Sullivan Michael J	Thick Outer Cover Layer Golf Ball
CN102786458B (zh) *	2012-06-04	2014-02-12	天津渤海职业技术学院	吡咯甲酰胺衍生物、其制备方法和用途
EP3097095A1 (fr) *	2014-01-24	2016-11-30	AbbVie Inc.	Dérivés furo-3-carboxamide et méthodes d'utilisation

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5750702A (en) *	1993-10-27	1998-05-12	Neurogen Corporation	Certain pyrrolo pyridine-3-carboxamides; a new class of GABA brain receptor ligands
US5484944A (en)	1993-10-27	1996-01-16	Neurogen Corporation	Certain fused pyrrolecarboxanilides and their use as GABA brain receptor ligands
US5804686A (en)	1996-01-19	1998-09-08	Neurogen Corporation	fused pyrrolecarboxamides; a new class of GABA brain receptor ligands
AU2218997A (en)	1996-03-22	1997-10-10	Neurogen Corporation	Certain fused pyrrolecarboxamides as gaba brain receptor ligands

1998
- 1998-10-21 JP JP2000521068A patent/JP3497469B2/ja not_active Expired - Fee Related
- 1998-10-21 CZ CZ20001769A patent/CZ20001769A3/cs unknown
- 1998-10-21 SK SK687-2000A patent/SK6872000A3/sk unknown
- 1998-10-21 HR HR20000298A patent/HRP20000298A2/hr not_active Application Discontinuation
- 1998-10-21 KR KR10-2000-7005185A patent/KR100386722B1/ko not_active Expired - Fee Related
- 1998-10-21 ID IDW20000893A patent/ID24135A/id unknown
- 1998-10-21 YU YU27300A patent/YU27300A/sh unknown
- 1998-10-21 PT PT98946678T patent/PT1030838E/pt unknown
- 1998-10-21 NZ NZ503916A patent/NZ503916A/xx unknown
- 1998-10-21 AU AU93639/98A patent/AU745788B2/en not_active Ceased
- 1998-10-21 EA EA200000413A patent/EA002243B1/ru not_active IP Right Cessation
- 1998-10-21 ES ES98946678T patent/ES2186232T3/es not_active Expired - Lifetime
- 1998-10-21 WO PCT/IB1998/001672 patent/WO1999025684A1/fr not_active Ceased
- 1998-10-21 PL PL98340554A patent/PL340554A1/xx not_active Application Discontinuation
- 1998-10-21 BR BR9814161-9A patent/BR9814161A/pt not_active Application Discontinuation
- 1998-10-21 EP EP98946678A patent/EP1030838B1/fr not_active Expired - Lifetime
- 1998-10-21 AT AT98946678T patent/ATE231492T1/de not_active IP Right Cessation
- 1998-10-21 CN CN98811119A patent/CN1280566A/zh active Pending
- 1998-10-21 IL IL13571098A patent/IL135710A0/xx unknown
- 1998-10-21 CN CNA031594727A patent/CN1508129A/zh active Pending
- 1998-10-21 TR TR2000/01343T patent/TR200001343T2/xx unknown
- 1998-10-21 CA CA002310095A patent/CA2310095A1/fr not_active Abandoned
- 1998-10-21 HU HU0100235A patent/HUP0100235A3/hu unknown
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- 1998-10-21 DK DK98946678T patent/DK1030838T3/da active
- 1998-10-21 DE DE69810959T patent/DE69810959T2/de not_active Expired - Fee Related
- 1998-11-10 PA PA19988462901A patent/PA8462901A1/es unknown
- 1998-11-10 TW TW087118708A patent/TW509675B/zh not_active IP Right Cessation
- 1998-11-11 TN TNTNSN98204A patent/TNSN98204A1/fr unknown
- 1998-11-11 MA MA25342A patent/MA24697A1/fr unknown
- 1998-11-11 DZ DZ980261A patent/DZ2651A1/fr active
- 1998-11-13 UY UY25249A patent/UY25249A1/es not_active IP Right Cessation
2000
- 2000-04-26 IS IS5469A patent/IS5469A/is unknown
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Also Published As

Publication number	Publication date
KR20010032063A (ko)	2001-04-16
DE69810959D1 (de)	2003-02-27
PA8462901A1 (es)	2000-05-24
PL340554A1 (en)	2001-02-12
AU9363998A (en)	1999-06-07
DE69810959T2 (de)	2003-06-05
CZ20001769A3 (cs)	2001-09-12
IS5469A (is)	2000-04-26
SK6872000A3 (en)	2002-02-05
KR100386722B1 (ko)	2003-06-09
HUP0100235A2 (hu)	2001-12-28
MA24697A1 (fr)	1999-07-01
IL135710A0 (en)	2001-05-20
HUP0100235A3 (en)	2002-04-29
CA2310095A1 (fr)	1999-05-27
WO1999025684A1 (fr)	1999-05-27
YU27300A (sh)	2002-10-18
HRP20000298A2 (en)	2001-02-28
BR9814161A (pt)	2000-09-26
CN1508129A (zh)	2004-06-30
TW509675B (en)	2002-11-11
JP2001523660A (ja)	2001-11-27
EP1030838B1 (fr)	2003-01-22
ATE231492T1 (de)	2003-02-15
AU745788B2 (en)	2002-03-28
NZ503916A (en)	2002-08-28
ID24135A (id)	2000-07-06
DK1030838T3 (da)	2003-02-24
CN1280566A (zh)	2001-01-17
EA200000413A1 (ru)	2000-12-25
TNSN98204A1 (fr)	2005-03-15
US6262272B1 (en)	2001-07-17
BG104413A (en)	2001-02-28
DZ2651A1 (fr)	2003-03-15
PT1030838E (pt)	2003-03-31
ES2186232T3 (es)	2003-05-01
EA002243B1 (ru)	2002-02-28
UY25249A1 (es)	1999-07-19
TR200001343T2 (tr)	2001-02-21
NO20002214D0 (no)	2000-04-28
NO20002214L (no)	2000-05-12
EP1030838A1 (fr)	2000-08-30
OA11378A (en)	2004-01-27
JP3497469B2 (ja)	2004-02-16

Publication	Publication Date	Title
RU2225406C2 (ru)	2004-03-10	Алкил-пиперазинил бензоксазолоновые и алкил-пиперидинил бензоксазолоновые производные, способ их получения и способ лечения
US7595338B2 (en)	2009-09-29	Process for preparing 3,3-disubstituted oxindoles and thio-oxindoles
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