IL140586A - Phenyl ester derivatives of a-amino acid and pharmaceuticals containing them - Google Patents

Phenyl ester derivatives of a-amino acid and pharmaceuticals containing them

Info

Publication number: IL140586A
Authority: IL; Israel
Prior art keywords: acid; amino acid; alkoxy; alkyl; acid phenyl
Prior art date: 1998-07-22

Application number

IL14058699A

Other languages

English (en)

Hebrew (he)

Other versions

IL140586A0 (en

Original Assignee

Akzo Nobel Nv

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.)

1998-07-22

Filing date

1999-07-16

Publication date

2004-06-01

1999-07-16 Application filed by Akzo Nobel Nv filed Critical Akzo Nobel Nv

2002-02-10 Publication of IL140586A0 publication Critical patent/IL140586A0/xx

2004-06-01 Publication of IL140586A publication Critical patent/IL140586A/en

Links

-1 alpha-AMINO ACID PHENYL ESTER Chemical class 0.000 title claims abstract description 51
239000008194 pharmaceutical composition Substances 0.000 title claims description 8
235000008206 alpha-amino acids Nutrition 0.000 title claims description 4
150000001875 compounds Chemical class 0.000 claims abstract description 45
150000003839 salts Chemical class 0.000 claims abstract description 30
125000000217 alkyl group Chemical group 0.000 claims abstract description 17
125000003342 alkenyl group Chemical group 0.000 claims abstract description 11
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 10
239000001257 hydrogen Substances 0.000 claims abstract description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims abstract description 7
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 5
125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims abstract description 3
125000003545 alkoxy group Chemical group 0.000 claims abstract 14
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract 9
YMEHWISYYMKMFO-WOMRJYOTSA-N methyl N-[(12E,15S)-15-[(4S)-4-(3-chlorophenyl)-2-oxopiperidin-1-yl]-9-oxo-8,17,19-triazatricyclo[14.2.1.02,7]nonadeca-1(18),2(7),3,5,12,16-hexaen-5-yl]carbamate Chemical compound COC(=O)Nc1ccc2-c3cnc([nH]3)[C@H](C\C=C\CCC(=O)Nc2c1)N1CC[C@@H](CC1=O)c1cccc(Cl)c1 YMEHWISYYMKMFO-WOMRJYOTSA-N 0.000 claims abstract 5
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 4
125000003710 aryl alkyl group Chemical group 0.000 claims abstract 4
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract 3
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims description 6
230000003444 anaesthetic effect Effects 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
229960003692 gamma aminobutyric acid Drugs 0.000 claims description 5
230000000694 effects Effects 0.000 claims description 4
125000000304 alkynyl group Chemical group 0.000 claims description 3
239000003814 drug Substances 0.000 claims description 3
125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
208000019901 Anxiety disease Diseases 0.000 claims description 2
201000009916 Postpartum depression Diseases 0.000 claims description 2
206010036618 Premenstrual syndrome Diseases 0.000 claims description 2
230000036506 anxiety Effects 0.000 claims description 2
201000010099 disease Diseases 0.000 claims description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
201000000484 premenstrual tension Diseases 0.000 claims description 2
239000000932 sedative agent Substances 0.000 claims description 2
230000001624 sedative effect Effects 0.000 claims description 2
208000019116 sleep disease Diseases 0.000 claims description 2
206010010904 Convulsion Diseases 0.000 claims 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
241000124008 Mammalia Species 0.000 claims 1
150000001371 alpha-amino acids Chemical class 0.000 claims 1
230000000202 analgesic effect Effects 0.000 claims 1
230000001939 inductive effect Effects 0.000 claims 1
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 50
239000002253 acid Substances 0.000 description 46
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
150000002500 ions Chemical class 0.000 description 37
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
238000005481 NMR spectroscopy Methods 0.000 description 35
238000005160 1H NMR spectroscopy Methods 0.000 description 25
JUJWROOIHBZHMG-RALIUCGRSA-N pyridine-d5 Chemical compound [2H]C1=NC([2H])=C([2H])C([2H])=C1[2H] JUJWROOIHBZHMG-RALIUCGRSA-N 0.000 description 25
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 24
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 22
239000000203 mixture Substances 0.000 description 21
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 13
150000002148 esters Chemical class 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
229960004132 diethyl ether Drugs 0.000 description 11
235000019260 propionic acid Nutrition 0.000 description 11
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 11
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
230000000147 hypnotic effect Effects 0.000 description 9
239000007787 solid Substances 0.000 description 9
239000002904 solvent Substances 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
125000004432 carbon atom Chemical group C* 0.000 description 8
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 description 7
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 7
KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
238000004587 chromatography analysis Methods 0.000 description 6
238000001990 intravenous administration Methods 0.000 description 6
238000000034 method Methods 0.000 description 6
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
239000012043 crude product Substances 0.000 description 5
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
229910000029 sodium carbonate Inorganic materials 0.000 description 5
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
MONMFXREYOKQTI-REOHCLBHSA-N (2s)-2-bromopropanoic acid Chemical compound C[C@H](Br)C(O)=O MONMFXREYOKQTI-REOHCLBHSA-N 0.000 description 4
PBIUDEUWYGBHDW-UHFFFAOYSA-N 2-chloro-1-pyridin-3-ylethanone;hydrochloride Chemical class Cl.ClCC(=O)C1=CC=CN=C1 PBIUDEUWYGBHDW-UHFFFAOYSA-N 0.000 description 4
WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 4
102000027484 GABAA receptors Human genes 0.000 description 4
108091008681 GABAA receptors Proteins 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 4
125000001246 bromo group Chemical group Br* 0.000 description 4
238000009833 condensation Methods 0.000 description 4
230000005494 condensation Effects 0.000 description 4
239000003480 eluent Substances 0.000 description 4
239000000284 extract Substances 0.000 description 4
239000003326 hypnotic agent Substances 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
229940086542 triethylamine Drugs 0.000 description 4
NNFDHJQLIFECSR-UHFFFAOYSA-N 2-bromo-4-methylpentanoic acid Chemical compound CC(C)CC(Br)C(O)=O NNFDHJQLIFECSR-UHFFFAOYSA-N 0.000 description 3
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
206010002091 Anaesthesia Diseases 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
239000013543 active substance Substances 0.000 description 3
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
238000001949 anaesthesia Methods 0.000 description 3
230000037005 anaesthesia Effects 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
150000002989 phenols Chemical class 0.000 description 3
239000000725 suspension Substances 0.000 description 3
LZHDLUQYWJYIKI-UHFFFAOYSA-N (2,6-dimethoxyphenyl) 2-(diethylamino)butanoate Chemical compound CCN(CC)C(CC)C(=O)OC1=C(OC)C=CC=C1OC LZHDLUQYWJYIKI-UHFFFAOYSA-N 0.000 description 2
QCQWVVNWUYVAGV-UHFFFAOYSA-N (2,6-dimethoxyphenyl) 2-morpholin-4-ylpropanoate Chemical compound COC1=CC=CC(OC)=C1OC(=O)C(C)N1CCOCC1 QCQWVVNWUYVAGV-UHFFFAOYSA-N 0.000 description 2
ZFBNNSOJNZBLLS-UHFFFAOYSA-N 2,6-Dimethoxy-4-methylphenol Chemical compound COC1=CC(C)=CC(OC)=C1O ZFBNNSOJNZBLLS-UHFFFAOYSA-N 0.000 description 2
YUXJYMYWKQCNFV-UHFFFAOYSA-N 2-[methyl(2-phenylethyl)amino]propanoic acid Chemical compound OC(=O)C(C)N(C)CCC1=CC=CC=C1 YUXJYMYWKQCNFV-UHFFFAOYSA-N 0.000 description 2
IQGRVWSONWFJJD-UHFFFAOYSA-N 2-bromo-4-methylpentanoyl chloride Chemical compound CC(C)CC(Br)C(Cl)=O IQGRVWSONWFJJD-UHFFFAOYSA-N 0.000 description 2
YAQLSKVCTLCIIE-UHFFFAOYSA-N 2-bromobutyric acid Chemical compound CCC(Br)C(O)=O YAQLSKVCTLCIIE-UHFFFAOYSA-N 0.000 description 2
IBZKBSXREAQDTO-UHFFFAOYSA-N 2-methoxy-n-(2-methoxyethyl)ethanamine Chemical compound COCCNCCOC IBZKBSXREAQDTO-UHFFFAOYSA-N 0.000 description 2
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
VTBHBNXGFPTBJL-UHFFFAOYSA-N 4-tert-butyl-1-sulfanylidene-2,6,7-trioxa-1$l^{5}-phosphabicyclo[2.2.2]octane Chemical compound C1OP2(=S)OCC1(C(C)(C)C)CO2 VTBHBNXGFPTBJL-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
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JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/38—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to acyclic carbon atoms and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
- C07C229/12—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of acyclic carbon skeletons
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P23/00—Anaesthetics
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- 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
- A61P25/20—Hypnotics; Sedatives
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
- C07C229/16—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of hydrocarbon radicals substituted by amino or carboxyl groups, e.g. ethylenediamine-tetra-acetic acid, iminodiacetic acids

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Pain & Pain Management (AREA)
Anesthesiology (AREA)
Psychiatry (AREA)
Rheumatology (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

IL14058699A 1998-07-22 1999-07-16 Phenyl ester derivatives of a-amino acid and pharmaceuticals containing them IL140586A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP98305837		1998-07-22
PCT/EP1999/005051 WO2000005196A1 (en)	1998-07-22	1999-07-16	α-AMINO ACID PHENYL ESTER DERIVATIVES

Publications (2)

Publication Number	Publication Date
IL140586A0 IL140586A0 (en)	2002-02-10
IL140586A true IL140586A (en)	2004-06-01

Family

ID=8234960

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL14058699A IL140586A (en)	1998-07-22	1999-07-16	Phenyl ester derivatives of a-amino acid and pharmaceuticals containing them

Country Status (27)

Country	Link
US (1)	US6451854B1 (de)
EP (1)	EP1098871B1 (de)
JP (1)	JP2002521358A (de)
KR (1)	KR100599142B1 (de)
CN (1)	CN1183101C (de)
AR (1)	AR021165A1 (de)
AT (1)	ATE244697T1 (de)
AU (1)	AU758808B2 (de)
BR (1)	BR9912291A (de)
CA (1)	CA2337945A1 (de)
CO (1)	CO5080742A1 (de)
DE (1)	DE69909486T2 (de)
DK (1)	DK1098871T3 (de)
ES (1)	ES2203163T3 (de)
HU (1)	HUP0102705A3 (de)
ID (1)	ID27261A (de)
IL (1)	IL140586A (de)
NO (1)	NO20010280L (de)
NZ (1)	NZ509327A (de)
PE (1)	PE20000880A1 (de)
PL (1)	PL345621A1 (de)
PT (1)	PT1098871E (de)
RU (1)	RU2223947C2 (de)
SK (1)	SK1032001A3 (de)
TR (1)	TR200100166T2 (de)
TW (1)	TW565546B (de)
WO (1)	WO2000005196A1 (de)

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AR031473A1 (es) *	2000-11-20	2003-09-24	Lundbeck & Co As H	Intensificadores de gaba en el tratamiento de enfermedades relacionadas con una reducida actividad neuroesteroide
DE60212101T2 (de)	2001-01-19	2006-11-23	Akzo Nobel N.V.	Alanin-2,6-dialkoxyphenylesterderivate als hypnotika
CN120965524B (zh) *	2025-10-21	2026-01-09	四川大学	一种(n,n-二甲基氨基)甲酸-4,5-二甲氧基-2-[(1e)-3-甲氧基-丙烯基]苯基酯化合物及其制备方法和应用

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1102011A (en) *	1964-05-21	1968-02-07	Richardson Merrell Spa	Phenol esters of amino acids
GB1160468A (en)	1967-05-08	1969-08-06	May & Baker Ltd	Morpholine Derivative
SU495828A3 (ru) *	1972-10-12	1975-12-15	Ф.Гоффманн-Ля Рош И Ко Аг. (Фирма)	Способ получени мета-производных бензойной кислоты

1999
- 1999-07-16 ID IDW20010160A patent/ID27261A/id unknown
- 1999-07-16 CN CNB998091308A patent/CN1183101C/zh not_active Expired - Fee Related
- 1999-07-16 HU HU0102705A patent/HUP0102705A3/hu unknown
- 1999-07-16 KR KR1020017000592A patent/KR100599142B1/ko not_active Expired - Fee Related
- 1999-07-16 IL IL14058699A patent/IL140586A/en not_active IP Right Cessation
- 1999-07-16 ES ES99936544T patent/ES2203163T3/es not_active Expired - Lifetime
- 1999-07-16 TR TR2001/00166T patent/TR200100166T2/xx unknown
- 1999-07-16 WO PCT/EP1999/005051 patent/WO2000005196A1/en not_active Ceased
- 1999-07-16 AU AU51602/99A patent/AU758808B2/en not_active Ceased
- 1999-07-16 EP EP99936544A patent/EP1098871B1/de not_active Expired - Lifetime
- 1999-07-16 US US09/744,004 patent/US6451854B1/en not_active Expired - Fee Related
- 1999-07-16 AT AT99936544T patent/ATE244697T1/de not_active IP Right Cessation
- 1999-07-16 CA CA002337945A patent/CA2337945A1/en not_active Abandoned
- 1999-07-16 PL PL99345621A patent/PL345621A1/xx not_active IP Right Cessation
- 1999-07-16 DE DE69909486T patent/DE69909486T2/de not_active Expired - Fee Related
- 1999-07-16 JP JP2000561153A patent/JP2002521358A/ja active Pending
- 1999-07-16 RU RU2001104896/04A patent/RU2223947C2/ru not_active IP Right Cessation
- 1999-07-16 PT PT99936544T patent/PT1098871E/pt unknown
- 1999-07-16 BR BR9912291-0A patent/BR9912291A/pt not_active Application Discontinuation
- 1999-07-16 SK SK103-2001A patent/SK1032001A3/sk unknown
- 1999-07-16 NZ NZ509327A patent/NZ509327A/xx unknown
- 1999-07-16 DK DK99936544T patent/DK1098871T3/da active
- 1999-07-21 PE PE1999000731A patent/PE20000880A1/es not_active Application Discontinuation
- 1999-07-21 AR ARP990103567A patent/AR021165A1/es active IP Right Grant
- 1999-07-21 CO CO99045953A patent/CO5080742A1/es unknown
- 1999-07-23 TW TW088112565A patent/TW565546B/zh not_active IP Right Cessation
2001
- 2001-01-17 NO NO20010280A patent/NO20010280L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
CO5080742A1 (es)	2001-09-25
PL345621A1 (en)	2002-01-02
EP1098871A1 (de)	2001-05-16
TR200100166T2 (tr)	2001-05-21
HUP0102705A2 (hu)	2001-12-28
SK1032001A3 (en)	2001-08-06
ATE244697T1 (de)	2003-07-15
EP1098871B1 (de)	2003-07-09
ID27261A (id)	2001-03-22
ES2203163T3 (es)	2004-04-01
CA2337945A1 (en)	2000-02-03
DE69909486T2 (de)	2004-05-27
NZ509327A (en)	2003-04-29
AU5160299A (en)	2000-02-14
NO20010280D0 (no)	2001-01-17
AR021165A1 (es)	2002-07-03
AU758808B2 (en)	2003-03-27
TW565546B (en)	2003-12-11
BR9912291A (pt)	2001-04-17
CN1311770A (zh)	2001-09-05
US6451854B1 (en)	2002-09-17
KR20010071905A (ko)	2001-07-31
PT1098871E (pt)	2003-11-28
DE69909486D1 (de)	2003-08-14
DK1098871T3 (da)	2003-10-27
PE20000880A1 (es)	2000-09-12
NO20010280L (no)	2001-03-08
RU2223947C2 (ru)	2004-02-20
JP2002521358A (ja)	2002-07-16
HUP0102705A3 (en)	2002-11-28
IL140586A0 (en)	2002-02-10
WO2000005196A1 (en)	2000-02-03
KR100599142B1 (ko)	2006-07-12
CN1183101C (zh)	2005-01-05

Legal Events

Date	Code	Title
2004-11-10	FF	Patent granted
2005-09-25	KB	Patent renewed
2010-10-31	MM9K	Patent not in force due to non-payment of renewal fees

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