KR20100072287A - 페닐피롤리딘 화합물 - Google Patents
페닐피롤리딘 화합물 Download PDFInfo
- Publication number
- KR20100072287A KR20100072287A KR1020107008900A KR20107008900A KR20100072287A KR 20100072287 A KR20100072287 A KR 20100072287A KR 1020107008900 A KR1020107008900 A KR 1020107008900A KR 20107008900 A KR20107008900 A KR 20107008900A KR 20100072287 A KR20100072287 A KR 20100072287A
- Authority
- KR
- South Korea
- Prior art keywords
- pyrrolidin
- methoxy
- phenyl
- disorders
- melatonin
- Prior art date
- Legal status (The legal status 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 status listed.)
- Withdrawn
Links
- VDQQJMHXZCMNMU-UHFFFAOYSA-N 1-phenylpyrrolidine Chemical class C1CCCN1C1=CC=CC=C1 VDQQJMHXZCMNMU-UHFFFAOYSA-N 0.000 title abstract description 4
- YJPIGAIKUZMOQA-UHFFFAOYSA-N Melatonin Natural products COC1=CC=C2N(C(C)=O)C=C(CCN)C2=C1 YJPIGAIKUZMOQA-UHFFFAOYSA-N 0.000 claims abstract description 17
- DRLFMBDRBRZALE-UHFFFAOYSA-N melatonin Chemical compound COC1=CC=C2NC=C(CCNC(C)=O)C2=C1 DRLFMBDRBRZALE-UHFFFAOYSA-N 0.000 claims abstract description 17
- 229960003987 melatonin Drugs 0.000 claims abstract description 17
- 150000001875 compounds Chemical class 0.000 claims description 38
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 33
- 208000035475 disorder Diseases 0.000 claims description 25
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims description 18
- 206010022437 insomnia Diseases 0.000 claims description 18
- 230000007170 pathology Effects 0.000 claims description 16
- 208000024827 Alzheimer disease Diseases 0.000 claims description 14
- 210000004556 brain Anatomy 0.000 claims description 11
- -1 phenylpyrrolidine compound Chemical class 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 9
- 208000019888 Circadian rhythm sleep disease Diseases 0.000 claims description 8
- 208000001456 Jet Lag Syndrome Diseases 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 8
- 208000033915 jet lag type circadian rhythm sleep disease Diseases 0.000 claims description 8
- 208000019116 sleep disease Diseases 0.000 claims description 8
- 208000000044 Amnesia Diseases 0.000 claims description 7
- 208000019901 Anxiety disease Diseases 0.000 claims description 7
- 208000027559 Appetite disease Diseases 0.000 claims description 7
- 208000027534 Emotional disease Diseases 0.000 claims description 7
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 7
- 208000026139 Memory disease Diseases 0.000 claims description 7
- 208000019695 Migraine disease Diseases 0.000 claims description 7
- 208000008589 Obesity Diseases 0.000 claims description 7
- 206010033664 Panic attack Diseases 0.000 claims description 7
- 206010039966 Senile dementia Diseases 0.000 claims description 7
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- 206010012601 diabetes mellitus Diseases 0.000 claims description 7
- 230000002526 effect on cardiovascular system Effects 0.000 claims description 7
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- MMQIUWHHXFUGAP-VUWPPUDQSA-N (2s)-2-fluoro-n-[1-(3-methoxyphenyl)pyrrolidin-3-yl]propanamide Chemical compound COC1=CC=CC(N2CC(CC2)NC(=O)[C@H](C)F)=C1 MMQIUWHHXFUGAP-VUWPPUDQSA-N 0.000 claims description 2
- LRSLJDKEWRAQMZ-LLVKDONJSA-N 1-[(3s)-1-(3-methoxyphenyl)pyrrolidin-3-yl]cyclopropane-1-carboxamide Chemical compound COC1=CC=CC(N2C[C@@H](CC2)C2(CC2)C(N)=O)=C1 LRSLJDKEWRAQMZ-LLVKDONJSA-N 0.000 claims description 2
- RDVWEXSYTNNSLM-NSHDSACASA-N 1-ethyl-3-[(3s)-1-(3-methoxyphenyl)pyrrolidin-3-yl]urea Chemical compound C1[C@@H](NC(=O)NCC)CCN1C1=CC=CC(OC)=C1 RDVWEXSYTNNSLM-NSHDSACASA-N 0.000 claims description 2
- ZYCJOIXTTRTPPP-VIFPVBQESA-N 2,2,2-trifluoro-n-[(3s)-1-(3-methoxyphenyl)pyrrolidin-3-yl]acetamide Chemical compound COC1=CC=CC(N2C[C@H](CC2)NC(=O)C(F)(F)F)=C1 ZYCJOIXTTRTPPP-VIFPVBQESA-N 0.000 claims description 2
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- UJYFWBHTOBRJNK-LBPRGKRZSA-N n-[(3s)-1-(3-methoxyphenyl)pyrrolidin-3-yl]-2,2-dimethylpropanamide Chemical compound COC1=CC=CC(N2C[C@H](CC2)NC(=O)C(C)(C)C)=C1 UJYFWBHTOBRJNK-LBPRGKRZSA-N 0.000 claims description 2
- KUOOFEYJCRNFOO-LBPRGKRZSA-N n-[(3s)-1-(3-methoxyphenyl)pyrrolidin-3-yl]-2-methylpropanamide Chemical compound COC1=CC=CC(N2C[C@H](CC2)NC(=O)C(C)C)=C1 KUOOFEYJCRNFOO-LBPRGKRZSA-N 0.000 claims description 2
- KNVMZTZPDNRYEJ-ZDUSSCGKSA-N n-[(3s)-1-(3-methoxyphenyl)pyrrolidin-3-yl]-3-methylbutanamide Chemical compound COC1=CC=CC(N2C[C@H](CC2)NC(=O)CC(C)C)=C1 KNVMZTZPDNRYEJ-ZDUSSCGKSA-N 0.000 claims description 2
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- YHIPILPTUVMWQT-UHFFFAOYSA-N Oplophorus luciferin Chemical compound C1=CC(O)=CC=C1CC(C(N1C=C(N2)C=3C=CC(O)=CC=3)=O)=NC1=C2CC1=CC=CC=C1 YHIPILPTUVMWQT-UHFFFAOYSA-N 0.000 description 6
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- ASHGTJPOSUFTGB-UHFFFAOYSA-N 3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1 ASHGTJPOSUFTGB-UHFFFAOYSA-N 0.000 description 5
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
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- 239000005060 rubber Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 208000020685 sleep-wake disease Diseases 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 210000000221 suprachiasmatic nucleus Anatomy 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000001360 synchronised effect Effects 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229960004559 theobromine Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
- C07D207/14—Nitrogen atoms not forming part of a nitro radical
-
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive 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
-
- 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
- A61P25/06—Antimigraine agents
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Emergency Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Anesthesiology (AREA)
- Psychology (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200702800A ES2331276B1 (es) | 2007-10-25 | 2007-10-25 | Compuestos de fenilpirrolidina. |
| ESP200702800 | 2007-10-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20100072287A true KR20100072287A (ko) | 2010-06-30 |
Family
ID=40291255
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020107008900A Withdrawn KR20100072287A (ko) | 2007-10-25 | 2008-10-23 | 페닐피롤리딘 화합물 |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US20120184594A1 (enExample) |
| EP (1) | EP2203422B1 (enExample) |
| JP (1) | JP2011500764A (enExample) |
| KR (1) | KR20100072287A (enExample) |
| CN (1) | CN101878198A (enExample) |
| AR (1) | AR069002A1 (enExample) |
| AT (1) | ATE513809T1 (enExample) |
| AU (1) | AU2008316473A1 (enExample) |
| BR (1) | BRPI0817660A2 (enExample) |
| CA (1) | CA2703458A1 (enExample) |
| CL (1) | CL2008003141A1 (enExample) |
| DK (1) | DK2203422T3 (enExample) |
| ES (2) | ES2331276B1 (enExample) |
| MX (1) | MX2010004469A (enExample) |
| PL (1) | PL2203422T3 (enExample) |
| PT (1) | PT2203422E (enExample) |
| RU (1) | RU2010120845A (enExample) |
| SI (1) | SI2203422T1 (enExample) |
| TW (1) | TW200920353A (enExample) |
| UY (1) | UY31425A1 (enExample) |
| WO (1) | WO2009053441A1 (enExample) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5753709A (en) * | 1995-06-07 | 1998-05-19 | Bristol-Myers Squibb Company | N-acyl-2 aryl cyclopropylmethylamine derivatives as melatonergics |
| DE60007745T2 (de) * | 1999-06-30 | 2005-03-10 | Bristol-Myers Squibb Co. | Heterocyclische aminopyrrolidon-derivate als melatonergene wirkstoffe |
-
2007
- 2007-10-25 ES ES200702800A patent/ES2331276B1/es not_active Withdrawn - After Issue
-
2008
- 2008-10-23 DK DK08842890.9T patent/DK2203422T3/da active
- 2008-10-23 AT AT08842890T patent/ATE513809T1/de active
- 2008-10-23 AR ARP080104616A patent/AR069002A1/es not_active Application Discontinuation
- 2008-10-23 BR BRPI0817660A patent/BRPI0817660A2/pt not_active IP Right Cessation
- 2008-10-23 SI SI200830368T patent/SI2203422T1/sl unknown
- 2008-10-23 EP EP08842890A patent/EP2203422B1/en not_active Not-in-force
- 2008-10-23 JP JP2010530463A patent/JP2011500764A/ja not_active Abandoned
- 2008-10-23 CN CN2008801131031A patent/CN101878198A/zh active Pending
- 2008-10-23 PL PL08842890T patent/PL2203422T3/pl unknown
- 2008-10-23 WO PCT/EP2008/064390 patent/WO2009053441A1/en not_active Ceased
- 2008-10-23 AU AU2008316473A patent/AU2008316473A1/en not_active Abandoned
- 2008-10-23 MX MX2010004469A patent/MX2010004469A/es active IP Right Grant
- 2008-10-23 US US12/739,708 patent/US20120184594A1/en not_active Abandoned
- 2008-10-23 PT PT08842890T patent/PT2203422E/pt unknown
- 2008-10-23 CA CA2703458A patent/CA2703458A1/en not_active Abandoned
- 2008-10-23 KR KR1020107008900A patent/KR20100072287A/ko not_active Withdrawn
- 2008-10-23 RU RU2010120845/04A patent/RU2010120845A/ru not_active Application Discontinuation
- 2008-10-23 ES ES08842890T patent/ES2368697T3/es active Active
- 2008-10-24 UY UY31425A patent/UY31425A1/es unknown
- 2008-10-24 TW TW097140810A patent/TW200920353A/zh unknown
- 2008-10-24 CL CL2008003141A patent/CL2008003141A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ATE513809T1 (de) | 2011-07-15 |
| EP2203422A1 (en) | 2010-07-07 |
| WO2009053441A1 (en) | 2009-04-30 |
| BRPI0817660A2 (pt) | 2015-09-29 |
| ES2331276A1 (es) | 2009-12-28 |
| PT2203422E (pt) | 2011-09-26 |
| CA2703458A1 (en) | 2009-04-30 |
| ES2368697T3 (es) | 2011-11-21 |
| ES2331276B1 (es) | 2010-10-21 |
| TW200920353A (en) | 2009-05-16 |
| UY31425A1 (es) | 2009-04-30 |
| SI2203422T1 (sl) | 2011-10-28 |
| CN101878198A (zh) | 2010-11-03 |
| PL2203422T3 (pl) | 2011-11-30 |
| AU2008316473A1 (en) | 2009-04-30 |
| US20120184594A1 (en) | 2012-07-19 |
| CL2008003141A1 (es) | 2009-03-06 |
| JP2011500764A (ja) | 2011-01-06 |
| RU2010120845A (ru) | 2011-11-27 |
| MX2010004469A (es) | 2010-07-06 |
| EP2203422B1 (en) | 2011-06-22 |
| AR069002A1 (es) | 2009-12-23 |
| DK2203422T3 (da) | 2011-10-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20100423 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |