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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Vascular Medicine (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Steroid 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 (https=) |
| EP (1) | EP1334094B1 (https=) |
| JP (1) | JP4012064B2 (https=) |
| KR (1) | KR100545430B1 (https=) |
| CN (1) | CN1261429C (https=) |
| AR (1) | AR034271A1 (https=) |
| AT (1) | ATE286042T1 (https=) |
| AU (2) | AU2002214029B2 (https=) |
| BR (1) | BR0115075A (https=) |
| CA (1) | CA2426009C (https=) |
| DE (1) | DE60108164T2 (https=) |
| DK (1) | DK1334094T3 (https=) |
| ES (1) | ES2233703T3 (https=) |
| GT (1) | GT200100220A (https=) |
| MX (1) | MXPA03003845A (https=) |
| PA (1) | PA8531601A1 (https=) |
| PE (1) | PE20020600A1 (https=) |
| PT (1) | PT1334094E (https=) |
| UY (1) | UY27009A1 (https=) |
| WO (1) | WO2002036584A1 (https=) |
| ZA (1) | ZA200302742B (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100566175B1 (ko) | 2000-08-16 | 2006-03-29 | 에프. 호프만-라 로슈 아게 | 신규한 아미노사이클로헥산 유도체 |
| 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 |
| JP2008544987A (ja) * | 2005-06-30 | 2008-12-11 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | 殺虫性の（二置換プロペニル）フェニルアルキル置換複素環式環を調製するための改善された方法 |
| FR2913019A1 (fr) * | 2007-02-23 | 2008-08-29 | Cerep Sa | Composes heterocycliques comme agents anti-neoplasiques ou inhibiteurs de proliferation cellulaire |
| 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 |
| WO2009069011A1 (en) * | 2007-11-29 | 2009-06-04 | Ranbaxy Laboratories Limited | Process for the preparation of substituted 1,3-oxathiolanes |
| CN103596570B (zh) * | 2010-12-27 | 2018-02-16 | 密苏里大学管委会 | 作为抗癌治疗的蛋白质靶的氧化鲨烯环化酶 |
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 (https=) * | 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 ES ES01982445T patent/ES2233703T3/es not_active Expired - Lifetime
- 2001-10-26 AU AU2002214029A patent/AU2002214029B2/en not_active Ceased
- 2001-10-26 CN CNB018182046A patent/CN1261429C/zh not_active Expired - Fee Related
- 2001-10-26 WO PCT/EP2001/012451 patent/WO2002036584A1/en not_active Ceased
- 2001-10-26 CA CA002426009A patent/CA2426009C/en not_active Expired - Fee Related
- 2001-10-26 AT AT01982445T patent/ATE286042T1/de active
- 2001-10-26 JP JP2002539343A patent/JP4012064B2/ja not_active Expired - Fee Related
- 2001-10-26 DK DK01982445T patent/DK1334094T3/da active
- 2001-10-26 MX MXPA03003845A patent/MXPA03003845A/es active IP Right Grant
- 2001-10-26 EP EP01982445A patent/EP1334094B1/en not_active Expired - Lifetime
- 2001-10-26 KR KR1020037006161A patent/KR100545430B1/ko not_active Expired - Fee Related
- 2001-10-26 AU AU1402902A patent/AU1402902A/xx active Pending
- 2001-10-26 DE DE60108164T patent/DE60108164T2/de not_active Expired - Lifetime
- 2001-10-26 PT PT01982445T patent/PT1334094E/pt unknown
- 2001-10-26 BR BR0115075-8A patent/BR0115075A/pt not_active Application Discontinuation
- 2001-10-30 PE PE2001001078A patent/PE20020600A1/es not_active Application Discontinuation
- 2001-10-31 GT GT200100220A patent/GT200100220A/es unknown
- 2001-10-31 US US09/999,424 patent/US6951879B2/en not_active Expired - Fee Related
- 2001-11-01 PA PA20018531601A patent/PA8531601A1/es unknown
- 2001-11-01 AR ARP010105115A patent/AR034271A1/es unknown
- 2001-11-01 UY UY27009A patent/UY27009A1/es not_active Application Discontinuation
-
2003
- 2003-04-08 ZA ZA200302742A patent/ZA200302742B/en unknown
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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 |
|---|---|
| CN1471522A (zh) | 2004-01-28 |
| EP1334094B1 (en) | 2004-12-29 |
| US7449483B2 (en) | 2008-11-11 |
| AU1402902A (en) | 2002-05-15 |
| CA2426009C (en) | 2008-10-07 |
| ATE286042T1 (de) | 2005-01-15 |
| CN1261429C (zh) | 2006-06-28 |
| EP1334094A1 (en) | 2003-08-13 |
| AR034271A1 (es) | 2004-02-18 |
| JP4012064B2 (ja) | 2007-11-21 |
| AU2002214029B2 (en) | 2004-12-23 |
| DE60108164D1 (de) | 2005-02-03 |
| US7173043B2 (en) | 2007-02-06 |
| KR100545430B1 (ko) | 2006-01-24 |
| US6951879B2 (en) | 2005-10-04 |
| US20020086891A1 (en) | 2002-07-04 |
| PA8531601A1 (es) | 2003-02-14 |
| CA2426009A1 (en) | 2002-05-10 |
| JP2004513124A (ja) | 2004-04-30 |
| US20070099985A1 (en) | 2007-05-03 |
| MXPA03003845A (es) | 2003-07-28 |
| US20050267200A1 (en) | 2005-12-01 |
| DK1334094T3 (da) | 2005-05-02 |
| BR0115075A (pt) | 2003-07-29 |
| KR20030045166A (ko) | 2003-06-09 |
| ES2233703T3 (es) | 2005-06-16 |
| DE60108164T2 (de) | 2006-03-02 |
| WO2002036584A1 (en) | 2002-05-10 |
| UY27009A1 (es) | 2002-06-20 |
| PE20020600A1 (es) | 2002-07-08 |
| GT200100220A (es) | 2002-07-04 |
| PT1334094E (pt) | 2005-05-31 |
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