KR20090023641A - 5-히드록시트립타민-6 리간드로서의 벤족사졸 및 벤조티아졸 유도체 - Google Patents
5-히드록시트립타민-6 리간드로서의 벤족사졸 및 벤조티아졸 유도체 Download PDFInfo
- Publication number
- KR20090023641A KR20090023641A KR1020087031621A KR20087031621A KR20090023641A KR 20090023641 A KR20090023641 A KR 20090023641A KR 1020087031621 A KR1020087031621 A KR 1020087031621A KR 20087031621 A KR20087031621 A KR 20087031621A KR 20090023641 A KR20090023641 A KR 20090023641A
- Authority
- KR
- South Korea
- Prior art keywords
- benzoxazole
- piperazin
- naphthylsulfonyl
- compound
- optionally substituted
- 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- Withdrawn
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- 239000003446 ligand Substances 0.000 title description 11
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 title description 10
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 140
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- 238000000034 method Methods 0.000 claims description 52
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 22
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
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- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 208000035475 disorder Diseases 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 13
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 10
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000002619 bicyclic group Chemical group 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
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- 125000005842 heteroatom Chemical group 0.000 claims description 7
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
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- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
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- 125000001624 naphthyl group Chemical group 0.000 claims description 4
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- OQLBUNURUSUBQN-UHFFFAOYSA-N 2-(4-cyclobutylpiperazin-1-yl)-4-naphthalen-1-ylsulfonyl-1,3-benzoxazole Chemical compound C=1C=CC2=CC=CC=C2C=1S(=O)(=O)C(C=1N=2)=CC=CC=1OC=2N(CC1)CCN1C1CCC1 OQLBUNURUSUBQN-UHFFFAOYSA-N 0.000 claims description 2
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- VRQZVFGHYLFLHY-UHFFFAOYSA-N 2-(4-methylpiperazin-1-yl)-4-naphthalen-1-ylsulfonyl-1,3-benzoxazole Chemical compound C1CN(C)CCN1C1=NC2=C(S(=O)(=O)C=3C4=CC=CC=C4C=CC=3)C=CC=C2O1 VRQZVFGHYLFLHY-UHFFFAOYSA-N 0.000 claims description 2
- WYXFCADKRYUNOI-UHFFFAOYSA-N 2-(4-methylpiperazin-1-yl)-5-naphthalen-1-ylsulfonyl-1,3-benzoxazole Chemical compound C1CN(C)CCN1C1=NC2=CC(S(=O)(=O)C=3C4=CC=CC=C4C=CC=3)=CC=C2O1 WYXFCADKRYUNOI-UHFFFAOYSA-N 0.000 claims description 2
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- ZTTWYNIORHZZGX-UHFFFAOYSA-N 2-piperazin-1-yl-4-[3-(trifluoromethyl)phenyl]sulfonyl-1,3-benzoxazole Chemical compound FC(F)(F)C1=CC=CC(S(=O)(=O)C=2C=3N=C(OC=3C=CC=2)N2CCNCC2)=C1 ZTTWYNIORHZZGX-UHFFFAOYSA-N 0.000 claims description 2
- MNJYTCUEXKDBRM-UHFFFAOYSA-N 2-piperazin-1-yl-7-(4-propan-2-ylphenyl)sulfonyl-1,3-benzoxazole Chemical compound C1=CC(C(C)C)=CC=C1S(=O)(=O)C1=CC=CC2=C1OC(N1CCNCC1)=N2 MNJYTCUEXKDBRM-UHFFFAOYSA-N 0.000 claims description 2
- UQNAGBJCCFFANN-UHFFFAOYSA-N 2-piperazin-1-yl-7-[3-(trifluoromethyl)phenyl]sulfonyl-1,3-benzoxazole Chemical compound FC(F)(F)C1=CC=CC(S(=O)(=O)C=2C=3OC(=NC=3C=CC=2)N2CCNCC2)=C1 UQNAGBJCCFFANN-UHFFFAOYSA-N 0.000 claims description 2
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- MFSZLULDGKDJNK-UHFFFAOYSA-N 4-(3-chlorophenyl)sulfonyl-2-piperazin-1-yl-1,3-benzoxazole Chemical compound ClC1=CC=CC(S(=O)(=O)C=2C=3N=C(OC=3C=CC=2)N2CCNCC2)=C1 MFSZLULDGKDJNK-UHFFFAOYSA-N 0.000 claims description 2
- XLODRHINUUOPLQ-UHFFFAOYSA-N 4-(3-fluorophenyl)sulfonyl-2-piperazin-1-yl-1,3-benzoxazole Chemical compound FC1=CC=CC(S(=O)(=O)C=2C=3N=C(OC=3C=CC=2)N2CCNCC2)=C1 XLODRHINUUOPLQ-UHFFFAOYSA-N 0.000 claims description 2
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- 150000002540 isothiocyanates Chemical class 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 230000004807 localization Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- 108020004999 messenger RNA Proteins 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000004220 muscle function Effects 0.000 description 1
- ZUHZZVMEUAUWHY-UHFFFAOYSA-N n,n-dimethylpropan-1-amine Chemical compound CCCN(C)C ZUHZZVMEUAUWHY-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 210000001577 neostriatum Anatomy 0.000 description 1
- 230000001722 neurochemical effect Effects 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 230000000626 neurodegenerative effect Effects 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
- 229960002748 norepinephrine Drugs 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 239000002953 phosphate buffered saline Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920006316 polyvinylpyrrolidine Polymers 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- OKBMCNHOEMXPTM-UHFFFAOYSA-M potassium peroxymonosulfate Chemical compound [K+].OOS([O-])(=O)=O OKBMCNHOEMXPTM-UHFFFAOYSA-M 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 229940071643 prefilled syringe Drugs 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000002287 radioligand Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 238000000611 regression analysis Methods 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 230000003362 replicative effect Effects 0.000 description 1
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- 238000007789 sealing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 231100000736 substance abuse Toxicity 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 239000007885 tablet disintegrant Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical group CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles 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 in position 2
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
- A61K31/423—Oxazoles condensed with carbocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/428—Thiazoles condensed with carbocyclic rings
-
- 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
- A61P25/28—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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
- C07D277/82—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurosurgery (AREA)
- Epidemiology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US80999606P | 2006-06-01 | 2006-06-01 | |
| US60/809,996 | 2006-06-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20090023641A true KR20090023641A (ko) | 2009-03-05 |
Family
ID=38668755
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020087031621A Withdrawn KR20090023641A (ko) | 2006-06-01 | 2007-05-25 | 5-히드록시트립타민-6 리간드로서의 벤족사졸 및 벤조티아졸 유도체 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US7501421B2 (enExample) |
| EP (1) | EP2024348A2 (enExample) |
| JP (1) | JP2009538909A (enExample) |
| KR (1) | KR20090023641A (enExample) |
| CN (1) | CN101490022A (enExample) |
| AR (1) | AR061147A1 (enExample) |
| AU (1) | AU2007255041A1 (enExample) |
| BR (1) | BRPI0712444A2 (enExample) |
| CA (1) | CA2659701A1 (enExample) |
| CR (1) | CR10474A (enExample) |
| EC (1) | ECSP088930A (enExample) |
| IL (1) | IL195590A0 (enExample) |
| MX (1) | MX2008015328A (enExample) |
| NO (1) | NO20085045L (enExample) |
| PE (1) | PE20080707A1 (enExample) |
| TW (1) | TW200804310A (enExample) |
| WO (1) | WO2007142904A2 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101250606B1 (ko) * | 2011-01-24 | 2013-04-03 | 이화여자대학교 산학협력단 | 5-ｈｔ６ 수용체 억제 작용을 갖는 신규한 벤조티아졸 및 벤즈이소티아졸유도체, 이의 제조 방법 및 이를 포함하는 약학적 조성물 |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG174125A1 (en) * | 2009-04-02 | 2011-10-28 | Merck Serono Sa | Dihydroorotate dehydrogenase inhibitors |
| US9890142B2 (en) | 2013-07-10 | 2018-02-13 | Meiji Seika Pharma Co., Ltd. | PDE4 inhibitor |
| AU2015286049B2 (en) | 2014-07-08 | 2018-03-01 | Sunshine Lake Pharma Co., Ltd. | Aromatic heterocyclic derivatives and pharmaceutical applications thereof |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7582635B2 (en) | 2002-12-24 | 2009-09-01 | Purdue Pharma, L.P. | Therapeutic agents useful for treating pain |
| GB0422263D0 (en) * | 2004-10-07 | 2004-11-10 | Glaxo Group Ltd | Novel compounds |
-
2007
- 2007-05-23 PE PE2007000635A patent/PE20080707A1/es not_active Application Discontinuation
- 2007-05-25 AU AU2007255041A patent/AU2007255041A1/en not_active Abandoned
- 2007-05-25 MX MX2008015328A patent/MX2008015328A/es not_active Application Discontinuation
- 2007-05-25 TW TW096118646A patent/TW200804310A/zh unknown
- 2007-05-25 KR KR1020087031621A patent/KR20090023641A/ko not_active Withdrawn
- 2007-05-25 CA CA002659701A patent/CA2659701A1/en not_active Abandoned
- 2007-05-25 BR BRPI0712444-9A patent/BRPI0712444A2/pt not_active Application Discontinuation
- 2007-05-25 WO PCT/US2007/012569 patent/WO2007142904A2/en not_active Ceased
- 2007-05-25 JP JP2009513221A patent/JP2009538909A/ja not_active Withdrawn
- 2007-05-25 EP EP07777299A patent/EP2024348A2/en not_active Withdrawn
- 2007-05-25 CN CNA2007800261442A patent/CN101490022A/zh active Pending
- 2007-05-31 AR ARP070102364A patent/AR061147A1/es unknown
- 2007-05-31 US US11/809,424 patent/US7501421B2/en not_active Expired - Fee Related
-
2008
- 2008-11-27 IL IL195590A patent/IL195590A0/en unknown
- 2008-12-01 EC EC2008008930A patent/ECSP088930A/es unknown
- 2008-12-01 CR CR10474A patent/CR10474A/es not_active Application Discontinuation
- 2008-12-03 NO NO20085045A patent/NO20085045L/no not_active Application Discontinuation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101250606B1 (ko) * | 2011-01-24 | 2013-04-03 | 이화여자대학교 산학협력단 | 5-ｈｔ６ 수용체 억제 작용을 갖는 신규한 벤조티아졸 및 벤즈이소티아졸유도체, 이의 제조 방법 및 이를 포함하는 약학적 조성물 |
Also Published As
| Publication number | Publication date |
|---|---|
| CR10474A (es) | 2009-01-07 |
| CN101490022A (zh) | 2009-07-22 |
| US7501421B2 (en) | 2009-03-10 |
| AR061147A1 (es) | 2008-08-06 |
| TW200804310A (en) | 2008-01-16 |
| JP2009538909A (ja) | 2009-11-12 |
| ECSP088930A (es) | 2009-01-30 |
| NO20085045L (no) | 2008-12-12 |
| BRPI0712444A2 (pt) | 2012-06-05 |
| PE20080707A1 (es) | 2008-05-22 |
| WO2007142904A2 (en) | 2007-12-13 |
| CA2659701A1 (en) | 2007-12-13 |
| WO2007142904A3 (en) | 2008-02-07 |
| US20070281945A1 (en) | 2007-12-06 |
| EP2024348A2 (en) | 2009-02-18 |
| AU2007255041A1 (en) | 2007-12-13 |
| MX2008015328A (es) | 2008-12-12 |
| IL195590A0 (en) | 2009-09-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20081226 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 |