ZA200302742B - Cholesterol lowering benzo(b) thiophenes and benzo(d) isothiazoles. - Google Patents
Cholesterol lowering benzo(b) thiophenes and benzo(d) isothiazoles. Download PDFInfo
- Publication number
- ZA200302742B ZA200302742B ZA200302742A ZA200302742A ZA200302742B ZA 200302742 B ZA200302742 B ZA 200302742B ZA 200302742 A ZA200302742 A ZA 200302742A ZA 200302742 A ZA200302742 A ZA 200302742A ZA 200302742 B ZA200302742 B ZA 200302742B
- Authority
- ZA
- South Africa
- Prior art keywords
- phenyl
- benzo
- methyl
- ethyl
- isothiazol
- Prior art date
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- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 title description 26
- 235000012000 cholesterol Nutrition 0.000 title description 11
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical class C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 title 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 129
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 54
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- 239000001257 hydrogen Substances 0.000 claims description 43
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 21
- 150000002148 esters Chemical class 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical group 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- -1 cyclopropyl-methylene Chemical group 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 238000011321 prophylaxis Methods 0.000 claims description 16
- 238000011282 treatment Methods 0.000 claims description 16
- 239000000460 chlorine Substances 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical group CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 6
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- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical group [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 6
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- IDPMLDMRHZRSJI-UHFFFAOYSA-N 2-[ethyl-[5-[3-[4-(trifluoromethyl)phenyl]-1,2-benzothiazol-6-yl]pent-4-ynyl]amino]ethanol Chemical compound N=1SC2=CC(C#CCCCN(CCO)CC)=CC=C2C=1C1=CC=C(C(F)(F)F)C=C1 IDPMLDMRHZRSJI-UHFFFAOYSA-N 0.000 claims description 3
- KCXINOJHQKHNHB-UHFFFAOYSA-N 3-(4-bromophenyl)-6-(3-piperidin-1-ylpropoxy)-1,2-benzothiazole Chemical compound C1=CC(Br)=CC=C1C1=NSC2=CC(OCCCN3CCCCC3)=CC=C12 KCXINOJHQKHNHB-UHFFFAOYSA-N 0.000 claims description 3
- GFBZAIYAMSYPFU-UHFFFAOYSA-N 3-(4-bromophenyl)-6-[4-(4-methylpiperazin-1-yl)butoxy]-1,2-benzothiazole Chemical compound C1CN(C)CCN1CCCCOC1=CC=C(C(=NS2)C=3C=CC(Br)=CC=3)C2=C1 GFBZAIYAMSYPFU-UHFFFAOYSA-N 0.000 claims description 3
- BCVITIXNZHVWAU-UHFFFAOYSA-N 5-[3-(4-bromophenyl)-1,2-benzothiazol-6-yl]-n,n-dimethylpent-4-yn-1-amine Chemical compound N=1SC2=CC(C#CCCCN(C)C)=CC=C2C=1C1=CC=C(Br)C=C1 BCVITIXNZHVWAU-UHFFFAOYSA-N 0.000 claims description 3
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- 125000005605 benzo group Chemical group 0.000 claims description 3
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- ASQVECKBMOMCER-UHFFFAOYSA-N n-ethyl-n-(2-methoxyethyl)-4-[(3-methyl-1,2-benzothiazol-6-yl)oxy]butan-1-amine Chemical compound COCCN(CC)CCCCOC1=CC=C2C(C)=NSC2=C1 ASQVECKBMOMCER-UHFFFAOYSA-N 0.000 description 1
- WHUADXBQHZMHBW-UHFFFAOYSA-N n-ethyl-n-(2-methoxyethyl)-4-[3-[4-(trifluoromethyl)phenyl]-1,2-benzothiazol-6-yl]but-3-yn-2-amine Chemical compound N=1SC2=CC(C#CC(C)N(CCOC)CC)=CC=C2C=1C1=CC=C(C(F)(F)F)C=C1 WHUADXBQHZMHBW-UHFFFAOYSA-N 0.000 description 1
- RKKBGMYODZPFHB-UHFFFAOYSA-N n-methyl-2-[[2-methyl-3-[4-(trifluoromethyl)phenyl]-1-benzothiophen-6-yl]oxy]ethanamine Chemical compound CC=1SC2=CC(OCCNC)=CC=C2C=1C1=CC=C(C(F)(F)F)C=C1 RKKBGMYODZPFHB-UHFFFAOYSA-N 0.000 description 1
- RFSUIFKIMNWWFB-UHFFFAOYSA-N n-methyl-3-[2-methyl-3-[4-(trifluoromethyl)phenyl]-1-benzothiophen-6-yl]-n-propylprop-2-yn-1-amine Chemical compound CC=1SC2=CC(C#CCN(C)CCC)=CC=C2C=1C1=CC=C(C(F)(F)F)C=C1 RFSUIFKIMNWWFB-UHFFFAOYSA-N 0.000 description 1
- FYQZPVYROITOCP-UHFFFAOYSA-N n-methyl-5-[2-methyl-3-[4-(trifluoromethyl)phenyl]-1-benzothiophen-6-yl]-n-propylpent-4-yn-1-amine Chemical compound CC=1SC2=CC(C#CCCCN(C)CCC)=CC=C2C=1C1=CC=C(C(F)(F)F)C=C1 FYQZPVYROITOCP-UHFFFAOYSA-N 0.000 description 1
- PVKYFHKZYNUHSB-UHFFFAOYSA-N n-methyl-n-[2-[[2-methyl-3-[4-(trifluoromethyl)phenyl]-1-benzothiophen-6-yl]oxy]ethyl]pyrimidin-4-amine Chemical compound C=1C=NC=NC=1N(C)CCOC(C=C1SC=2C)=CC=C1C=2C1=CC=C(C(F)(F)F)C=C1 PVKYFHKZYNUHSB-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 108020004017 nuclear receptors Proteins 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 230000002018 overexpression Effects 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- FYPMFJGVHOHGLL-UHFFFAOYSA-N probucol Chemical compound C=1C(C(C)(C)C)=C(O)C(C(C)(C)C)=CC=1SC(C)(C)SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 FYPMFJGVHOHGLL-UHFFFAOYSA-N 0.000 description 1
- 229960003912 probucol Drugs 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 235000018770 reduced food intake Nutrition 0.000 description 1
- 230000004141 reverse cholesterol transport Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 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
- 229960002855 simvastatin Drugs 0.000 description 1
- RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 238000011301 standard therapy Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- 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
- A61P3/06—Antihyperlipidemics
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
- C07D275/06—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to the ring sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Vascular Medicine (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP00123826 | 2000-11-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200302742B true ZA200302742B (en) | 2004-07-08 |
Family
ID=8170270
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200302742A ZA200302742B (en) | 2000-11-02 | 2003-04-08 | Cholesterol lowering benzo(b) thiophenes and benzo(d) isothiazoles. |
Country Status (21)
| Country | Link |
|---|---|
| US (3) | US6951879B2 (es) |
| EP (1) | EP1334094B1 (es) |
| JP (1) | JP4012064B2 (es) |
| KR (1) | KR100545430B1 (es) |
| CN (1) | CN1261429C (es) |
| AR (1) | AR034271A1 (es) |
| AT (1) | ATE286042T1 (es) |
| AU (2) | AU2002214029B2 (es) |
| BR (1) | BR0115075A (es) |
| CA (1) | CA2426009C (es) |
| DE (1) | DE60108164T2 (es) |
| DK (1) | DK1334094T3 (es) |
| ES (1) | ES2233703T3 (es) |
| GT (1) | GT200100220A (es) |
| MX (1) | MXPA03003845A (es) |
| PA (1) | PA8531601A1 (es) |
| PE (1) | PE20020600A1 (es) |
| PT (1) | PT1334094E (es) |
| UY (1) | UY27009A1 (es) |
| WO (1) | WO2002036584A1 (es) |
| ZA (1) | ZA200302742B (es) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL361783A1 (en) | 2000-08-16 | 2004-10-04 | F.Hoffmann-La Roche Ag | Novel aminocyclohexane derivatives |
| US7012077B2 (en) * | 2001-12-20 | 2006-03-14 | Hoffmann-La Roche Inc. | Substituted cyclohexane derivatives |
| EP1647549A1 (en) * | 2004-10-14 | 2006-04-19 | Laboratoire Theramex | Indazoles, benzisoxazoles and benzisothiazoles as estrogenic agents |
| US7446210B2 (en) * | 2004-10-26 | 2008-11-04 | Janssen Pharmaceutica N.V. | Factor Xa compounds |
| CN101213172A (zh) * | 2005-06-30 | 2008-07-02 | 拜尔农作物科学股份公司 | 具有杀虫作用的(二取代丙烯基)苯基烷基取代的杂环类化合物的改良的制备方法 |
| FR2913019A1 (fr) * | 2007-02-23 | 2008-08-29 | Cerep Sa | Composes heterocycliques comme agents anti-neoplasiques ou inhibiteurs de proliferation cellulaire |
| EP2225232B1 (en) * | 2007-11-29 | 2012-09-26 | Ranbaxy Laboratories Limited | Process for the preparation of substituted 1,3-oxathiolanes |
| CN101918416A (zh) * | 2007-11-29 | 2010-12-15 | 兰贝克赛实验室有限公司 | 制备取代的1,3-氧硫杂环戊烷,尤其是拉米夫定的方法和中间体 |
| EP2658544A4 (en) * | 2010-12-27 | 2014-05-28 | Univ Missouri | OXIDOSQUALENZYCASE AS A PROTEINT ARGET FOR ANTICIPATED THERAPEUTICS |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3598839A (en) * | 1969-06-30 | 1971-08-10 | Parke Davis & Co | Phenylbenzothiophene compounds |
| GR75101B (es) * | 1980-10-23 | 1984-07-13 | Pfizer | |
| GB8417559D0 (en) * | 1984-07-10 | 1984-08-15 | Pfizer Ltd | Anti-diarrhoeal agents |
| DE3905364A1 (de) | 1989-02-22 | 1990-08-23 | Hoechst Ag | Substituierte pyrimidin-derivate, verfahren zu ihrer herstellung und ihre verwendung als tool |
| EP0530149A1 (de) * | 1991-08-30 | 1993-03-03 | Ciba-Geigy Ag | Schädlingsbekämpfungsmittel |
| US5482949A (en) * | 1993-03-19 | 1996-01-09 | Eli Lilly And Company | Sulfonate derivatives of 3-aroylbenzo[b]thiophenes |
| CA2190699A1 (en) * | 1995-12-08 | 1997-06-09 | Johannes Aebi | Tertiary amines |
| CA2190708A1 (en) * | 1995-12-08 | 1997-06-09 | Johannes Aebi | Aminoalkyl substituted benzo-heterocyclic compounds |
| UA56197C2 (uk) | 1996-11-08 | 2003-05-15 | Зенека Лімітед | Гетероциклічні похідні |
-
2001
- 2001-10-26 CA CA002426009A patent/CA2426009C/en not_active Expired - Fee Related
- 2001-10-26 EP EP01982445A patent/EP1334094B1/en not_active Expired - Lifetime
- 2001-10-26 ES ES01982445T patent/ES2233703T3/es not_active Expired - Lifetime
- 2001-10-26 AU AU2002214029A patent/AU2002214029B2/en not_active Ceased
- 2001-10-26 AU AU1402902A patent/AU1402902A/xx active Pending
- 2001-10-26 PT PT01982445T patent/PT1334094E/pt unknown
- 2001-10-26 KR KR1020037006161A patent/KR100545430B1/ko not_active IP Right Cessation
- 2001-10-26 JP JP2002539343A patent/JP4012064B2/ja not_active Expired - Fee Related
- 2001-10-26 WO PCT/EP2001/012451 patent/WO2002036584A1/en active IP Right Grant
- 2001-10-26 DE DE60108164T patent/DE60108164T2/de not_active Expired - Lifetime
- 2001-10-26 DK DK01982445T patent/DK1334094T3/da active
- 2001-10-26 MX MXPA03003845A patent/MXPA03003845A/es active IP Right Grant
- 2001-10-26 BR BR0115075-8A patent/BR0115075A/pt not_active Application Discontinuation
- 2001-10-26 CN CNB018182046A patent/CN1261429C/zh not_active Expired - Fee Related
- 2001-10-26 AT AT01982445T patent/ATE286042T1/de active
- 2001-10-30 PE PE2001001078A patent/PE20020600A1/es not_active Application Discontinuation
- 2001-10-31 US US09/999,424 patent/US6951879B2/en not_active Expired - Fee Related
- 2001-10-31 GT GT200100220A patent/GT200100220A/es unknown
- 2001-11-01 AR ARP010105115A patent/AR034271A1/es unknown
- 2001-11-01 UY UY27009A patent/UY27009A1/es not_active Application Discontinuation
- 2001-11-01 PA PA20018531601A patent/PA8531601A1/es unknown
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2003
- 2003-04-08 ZA ZA200302742A patent/ZA200302742B/en unknown
-
2005
- 2005-07-08 US US11/178,164 patent/US7173043B2/en not_active Expired - Fee Related
-
2006
- 2006-12-06 US US11/634,573 patent/US7449483B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| PA8531601A1 (es) | 2003-02-14 |
| EP1334094B1 (en) | 2004-12-29 |
| GT200100220A (es) | 2002-07-04 |
| US20020086891A1 (en) | 2002-07-04 |
| KR20030045166A (ko) | 2003-06-09 |
| PT1334094E (pt) | 2005-05-31 |
| WO2002036584A1 (en) | 2002-05-10 |
| AR034271A1 (es) | 2004-02-18 |
| ES2233703T3 (es) | 2005-06-16 |
| JP2004513124A (ja) | 2004-04-30 |
| US6951879B2 (en) | 2005-10-04 |
| KR100545430B1 (ko) | 2006-01-24 |
| AU2002214029B2 (en) | 2004-12-23 |
| EP1334094A1 (en) | 2003-08-13 |
| MXPA03003845A (es) | 2003-07-28 |
| UY27009A1 (es) | 2002-06-20 |
| CA2426009A1 (en) | 2002-05-10 |
| CA2426009C (en) | 2008-10-07 |
| US20070099985A1 (en) | 2007-05-03 |
| DE60108164T2 (de) | 2006-03-02 |
| BR0115075A (pt) | 2003-07-29 |
| US7173043B2 (en) | 2007-02-06 |
| US20050267200A1 (en) | 2005-12-01 |
| DK1334094T3 (da) | 2005-05-02 |
| PE20020600A1 (es) | 2002-07-08 |
| US7449483B2 (en) | 2008-11-11 |
| CN1471522A (zh) | 2004-01-28 |
| DE60108164D1 (de) | 2005-02-03 |
| AU1402902A (en) | 2002-05-15 |
| JP4012064B2 (ja) | 2007-11-21 |
| ATE286042T1 (de) | 2005-01-15 |
| CN1261429C (zh) | 2006-06-28 |
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