DE60011801T2 - Benzoxa- und benzthiazolylsulfamate sowie ihre verwendung als steroid-sulfataseinhibitoren - Google Patents
Benzoxa- und benzthiazolylsulfamate sowie ihre verwendung als steroid-sulfataseinhibitoren Download PDFInfo
- Publication number
- DE60011801T2 DE60011801T2 DE60011801T DE60011801T DE60011801T2 DE 60011801 T2 DE60011801 T2 DE 60011801T2 DE 60011801 T DE60011801 T DE 60011801T DE 60011801 T DE60011801 T DE 60011801T DE 60011801 T2 DE60011801 T2 DE 60011801T2
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- formula
- compound
- benzoxazol
- salt
- 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.)
- Expired - Lifetime
Links
- AOSHFAMRFXBJCW-UHFFFAOYSA-N 1,3-benzothiazol-2-yl sulfamate Chemical compound S(N)(OC=1SC2=C(N=1)C=CC=C2)(=O)=O AOSHFAMRFXBJCW-UHFFFAOYSA-N 0.000 title 1
- 229940123142 Steroid sulfatase inhibitor Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 93
- -1 hexahydro-2,5-methanopentalenyl Chemical group 0.000 claims description 52
- 150000003839 salts Chemical class 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 10
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 8
- 125000005015 aryl alkynyl group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000005356 cycloalkylalkenyl group Chemical group 0.000 claims description 8
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 239000003085 diluting agent Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 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 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 4
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- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 20
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- 108010087999 Steryl-Sulfatase Proteins 0.000 description 19
- 239000003795 chemical substances by application Substances 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
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- 239000003112 inhibitor Substances 0.000 description 8
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- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 5
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
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- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
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- 150000002367 halogens Chemical class 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
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- 229920006395 saturated elastomer Polymers 0.000 description 4
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 3
- LLJMPRKYLLJAEB-UHFFFAOYSA-N 4-aminobenzene-1,3-diol;hydron;chloride Chemical compound Cl.NC1=CC=C(O)C=C1O LLJMPRKYLLJAEB-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- 206010028417 myasthenia gravis Diseases 0.000 description 1
- GBPIQZMLGLWMSS-UHFFFAOYSA-N n-(2,4-dihydroxyphenyl)-1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxamide Chemical compound C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(=O)NC1=CC=C(O)C=C1O GBPIQZMLGLWMSS-UHFFFAOYSA-N 0.000 description 1
- CMDYRFNDLFGGNM-UHFFFAOYSA-N n-(2,4-dihydroxyphenyl)-3,3,3-triphenylpropanamide Chemical compound OC1=CC(O)=CC=C1NC(=O)CC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 CMDYRFNDLFGGNM-UHFFFAOYSA-N 0.000 description 1
- AVFUIUJTGRPLGJ-UHFFFAOYSA-N n-(2,4-dihydroxyphenyl)-3,3-diphenylpropanamide Chemical compound OC1=CC(O)=CC=C1NC(=O)CC(C=1C=CC=CC=1)C1=CC=CC=C1 AVFUIUJTGRPLGJ-UHFFFAOYSA-N 0.000 description 1
- NMLIVJSOGSVTQI-UHFFFAOYSA-N n-(2,4-dihydroxyphenyl)adamantane-1-carboxamide Chemical compound OC1=CC(O)=CC=C1NC(=O)C1(C2)CC(C3)CC2CC3C1 NMLIVJSOGSVTQI-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 150000005845 steroid sulfates Chemical class 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000012089 stop solution Substances 0.000 description 1
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- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/04—Antipruritics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/08—Antiseborrheics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/10—Anti-acne agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
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- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- 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
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/14—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A61P5/28—Antiandrogens
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A61P5/32—Antioestrogens
-
- 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
-
- 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
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D263/57—Aryl or substituted aryl radicals
-
- 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
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Diabetes (AREA)
- Dermatology (AREA)
- Endocrinology (AREA)
- Immunology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Pulmonology (AREA)
- Heart & Thoracic Surgery (AREA)
- Psychiatry (AREA)
- Emergency Medicine (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Transplantation (AREA)
- Cardiology (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)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9927439.1A GB9927439D0 (en) | 1999-11-19 | 1999-11-19 | Organic compounds |
| GB9927439 | 1999-11-19 | ||
| GB0007511 | 2000-03-28 | ||
| GB0007511A GB0007511D0 (en) | 2000-03-28 | 2000-03-28 | Organic compounds |
| PCT/EP2000/011475 WO2001036398A1 (en) | 1999-11-19 | 2000-11-17 | Benzoxa- and benzthiazoles |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60011801D1 DE60011801D1 (de) | 2004-07-29 |
| DE60011801T2 true DE60011801T2 (de) | 2005-07-14 |
Family
ID=26243976
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60011801T Expired - Lifetime DE60011801T2 (de) | 1999-11-19 | 2000-11-17 | Benzoxa- und benzthiazolylsulfamate sowie ihre verwendung als steroid-sulfataseinhibitoren |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US6716865B1 (enExample) |
| EP (1) | EP1230227B1 (enExample) |
| JP (1) | JP2003514806A (enExample) |
| AR (1) | AR026504A1 (enExample) |
| AT (1) | ATE269853T1 (enExample) |
| AU (1) | AU1857701A (enExample) |
| CO (1) | CO5261573A1 (enExample) |
| DE (1) | DE60011801T2 (enExample) |
| DK (1) | DK1230227T3 (enExample) |
| ES (1) | ES2223620T3 (enExample) |
| HK (1) | HK1049329B (enExample) |
| PE (1) | PE20011012A1 (enExample) |
| PT (1) | PT1230227E (enExample) |
| TR (1) | TR200402432T4 (enExample) |
| WO (1) | WO2001036398A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR041952A1 (es) * | 2002-11-14 | 2005-06-01 | Novartis Ag | N-sulfonilaminotiazol |
| DE10260955A1 (de) * | 2002-12-20 | 2004-07-08 | Henkel Kgaa | Verwendung von Steroidsulfatase-Inhibitoren zur Verminderung von Haarausfall |
| RU2553476C2 (ru) * | 2007-08-02 | 2015-06-20 | Миллениум Фармасьютикалз, Инк. | Способ синтеза ингибиторов е1-активирующего фермента |
| CA2698814A1 (en) | 2007-09-17 | 2009-03-26 | Preglem S.A. | Treatment of oestrogen dependant conditions in pre-menopausal women |
| CN104926730B (zh) * | 2014-03-21 | 2017-07-21 | 中国科学院武汉岩土力学研究所 | 一种松香基咪唑啉类化合物及其合成方法和应用 |
| US11001564B2 (en) * | 2016-09-13 | 2021-05-11 | Arbutus Biopharma Corporation | Substituted chromane-8-carboxamide compounds and analogues thereof, and methods using same |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2868800A (en) | 1954-10-13 | 1959-01-13 | Upjohn Co | 6-ethoxybenzothiazole-2-sulfonamide |
| US4472418A (en) * | 1983-04-22 | 1984-09-18 | Merck & Co., Inc. | Benzothiazolesulfonamide derivatives for the topical treatment of elevated intraocular pressure |
| FI91869C (fi) | 1987-03-18 | 1994-08-25 | Tanabe Seiyaku Co | Menetelmä antidiabeettisena aineena käytettävien bensoksatsolijohdannaisten valmistamiseksi |
| US5273993A (en) | 1989-06-12 | 1993-12-28 | A. H. Robins Company, Incorporated | Compounds having one or more aminosulfonyloxy radicals useful as pharmaceuticals |
| PT94305B (pt) * | 1989-06-12 | 1997-02-28 | Robins Co Inc A H | Processo para a preparacao de compostos tendo um ou mais radicais aminossulfoniloxi uteis como produtos farmaceuticos |
| US5194446A (en) | 1989-06-12 | 1993-03-16 | A. H. Robins Company, Incorporated | Compounds having one or more aminosulfaonyloxy radicals useful as pharmaceuticals |
| US5192785A (en) | 1989-09-03 | 1993-03-09 | A. H. Robins Company, Incorporated | Sulfamates as antiglaucoma agents |
| AU658646B2 (en) | 1991-05-10 | 1995-04-27 | Rhone-Poulenc Rorer International (Holdings) Inc. | Bis mono-and bicyclic aryl and heteroaryl compounds which inhibit EGF and/or PDGF receptor tyrosine kinase |
| WO1993011120A1 (en) | 1991-11-27 | 1993-06-10 | Zynaxis Technologies, Incorporated | Compounds, compositions and methods for binding bio-affecting substances to surface membranes of bio-particles |
| CA2144763A1 (en) | 1992-10-14 | 1994-04-28 | George D. Hartman | Fibrinogen receptor antagonists |
| EP0785927B1 (en) | 1994-10-12 | 2003-08-27 | Euroceltique S.A. | Novel benzoxazoles |
| US6169085B1 (en) * | 1995-03-10 | 2001-01-02 | G. D. Searle & Company | Sulfonylalkanoylamino hydroxyethylamino sulfonamide retroviral protease inhibitors |
| US5677321A (en) | 1996-02-29 | 1997-10-14 | Synaptic Pharmaceutical Corporation | 5- and 6-(2-imidazolin-2-ylamino) and -(2-thiazolin-2-ylamino)-benzothiazoles as alpha-2 adrenergic ligands |
| US5709845A (en) | 1996-05-13 | 1998-01-20 | Rajagopalan; Raghavan | Tricyclic functional dyes for contrast enhancement in optical imaging |
| DE19653647A1 (de) | 1996-12-20 | 1998-06-25 | Hoechst Ag | Vitronectin - Rezeptorantagonisten, deren Herstellung sowie deren Verwendung |
| JPH10237053A (ja) | 1997-02-24 | 1998-09-08 | Sumitomo Chem Co Ltd | ベンゾチアゾール類の製造方法 |
| US6140051A (en) | 1997-07-21 | 2000-10-31 | Promega Biosciences, Inc. | Fluorescent dibenzazole derivatives and methods related thereto |
| GB2331988B (en) * | 1997-12-04 | 2003-04-16 | Imperial College | Polycyclic sulphamate inhibitors or oestrone sulphatase |
| GB9807779D0 (en) | 1998-04-09 | 1998-06-10 | Ciba Geigy Ag | Organic compounds |
| KR100597913B1 (ko) | 1998-06-18 | 2006-07-10 | 노파르티스 아게 | 벤즈아졸 화합물 및 그의 용도 |
-
2000
- 2000-11-03 CO CO00083906A patent/CO5261573A1/es not_active Application Discontinuation
- 2000-11-16 AR ARP000106055A patent/AR026504A1/es unknown
- 2000-11-17 ES ES00981270T patent/ES2223620T3/es not_active Expired - Lifetime
- 2000-11-17 AU AU18577/01A patent/AU1857701A/en not_active Abandoned
- 2000-11-17 PT PT00981270T patent/PT1230227E/pt unknown
- 2000-11-17 TR TR2004/02432T patent/TR200402432T4/xx unknown
- 2000-11-17 DE DE60011801T patent/DE60011801T2/de not_active Expired - Lifetime
- 2000-11-17 JP JP2001538887A patent/JP2003514806A/ja active Pending
- 2000-11-17 AT AT00981270T patent/ATE269853T1/de not_active IP Right Cessation
- 2000-11-17 EP EP00981270A patent/EP1230227B1/en not_active Expired - Lifetime
- 2000-11-17 WO PCT/EP2000/011475 patent/WO2001036398A1/en not_active Ceased
- 2000-11-17 DK DK00981270T patent/DK1230227T3/da active
- 2000-11-17 US US10/130,567 patent/US6716865B1/en not_active Expired - Fee Related
- 2000-11-17 HK HK02109307.7A patent/HK1049329B/en not_active IP Right Cessation
- 2000-11-17 PE PE2000001233A patent/PE20011012A1/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DE60011801D1 (de) | 2004-07-29 |
| WO2001036398A1 (en) | 2001-05-25 |
| CO5261573A1 (es) | 2003-03-31 |
| AU1857701A (en) | 2001-05-30 |
| PT1230227E (pt) | 2004-10-29 |
| US6716865B1 (en) | 2004-04-06 |
| ATE269853T1 (de) | 2004-07-15 |
| HK1049329B (en) | 2005-03-24 |
| HK1049329A1 (en) | 2003-05-09 |
| AR026504A1 (es) | 2003-02-12 |
| JP2003514806A (ja) | 2003-04-22 |
| EP1230227A1 (en) | 2002-08-14 |
| TR200402432T4 (tr) | 2004-12-21 |
| ES2223620T3 (es) | 2005-03-01 |
| PE20011012A1 (es) | 2001-10-02 |
| DK1230227T3 (da) | 2004-08-16 |
| EP1230227B1 (en) | 2004-06-23 |
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| 8364 | No opposition during term of opposition | ||
| 8328 | Change in the person/name/address of the agent |
Representative=s name: KROHER, STROBEL RECHTS- UND PATENTANWAELTE, 80336 |
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| 8328 | Change in the person/name/address of the agent |
Representative=s name: DR. SCHOEN & PARTNER, 80336 MUENCHEN |