ES2384118T3 - Derivados de 3,4-dihidro-3-amino-2H-1-benzopirano y -benzotiopirano como inhibidores de la dopamina-beta-hidroxilasa y métodos para su preparación - Google Patents
Derivados de 3,4-dihidro-3-amino-2H-1-benzopirano y -benzotiopirano como inhibidores de la dopamina-beta-hidroxilasa y métodos para su preparación Download PDFInfo
- Publication number
- ES2384118T3 ES2384118T3 ES07076123T ES07076123T ES2384118T3 ES 2384118 T3 ES2384118 T3 ES 2384118T3 ES 07076123 T ES07076123 T ES 07076123T ES 07076123 T ES07076123 T ES 07076123T ES 2384118 T3 ES2384118 T3 ES 2384118T3
- Authority
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- Spain
- Prior art keywords
- mmol
- compound
- ethyl acetate
- tert
- dihydroimidazol
- 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
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- 238000000034 method Methods 0.000 title description 21
- 239000003112 inhibitor Substances 0.000 title description 16
- 238000002360 preparation method Methods 0.000 title description 8
- 108010015720 Dopamine beta-Hydroxylase Proteins 0.000 title description 5
- 102100033156 Dopamine beta-hydroxylase Human genes 0.000 title description 5
- ONJRTQUWKRDCTA-UHFFFAOYSA-N 2h-thiochromene Chemical class C1=CC=C2C=CCSC2=C1 ONJRTQUWKRDCTA-UHFFFAOYSA-N 0.000 title description 2
- SVWDNDQOXZHBRM-UHFFFAOYSA-N 3,4-dihydro-2h-chromen-3-amine Chemical compound C1=CC=C2CC(N)COC2=C1 SVWDNDQOXZHBRM-UHFFFAOYSA-N 0.000 title description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 6
- 229910052717 sulfur Chemical group 0.000 claims abstract description 6
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 5
- 239000011737 fluorine Substances 0.000 claims abstract description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 4
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 3
- 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 abstract description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract 2
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- 229960002748 norepinephrine Drugs 0.000 description 25
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- 239000003085 diluting agent Substances 0.000 description 1
- MSJMDZAOKORVFC-SEPHDYHBSA-L disodium fumarate Chemical compound [Na+].[Na+].[O-]C(=O)\C=C\C([O-])=O MSJMDZAOKORVFC-SEPHDYHBSA-L 0.000 description 1
- AUZONCFQVSMFAP-UHFFFAOYSA-N disulfiram Chemical compound CCN(CC)C(=S)SSC(=S)N(CC)CC AUZONCFQVSMFAP-UHFFFAOYSA-N 0.000 description 1
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- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 230000000004 hemodynamic effect Effects 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
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- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
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- 229940073640 magnesium sulfate anhydrous Drugs 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
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- 210000004165 myocardium Anatomy 0.000 description 1
- ZCUORLRUJMTFOL-PFEQFJNWSA-N n-[(3r)-3-[4-(2-aminoethyl)-2-sulfanylidene-1h-imidazol-3-yl]-3,4-dihydro-2h-chromen-6-yl]acetamide;hydrochloride Chemical compound Cl.N1([C@H]2COC3=CC=C(C=C3C2)NC(=O)C)C(CCN)=CNC1=S ZCUORLRUJMTFOL-PFEQFJNWSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
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- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000005544 phthalimido group Chemical group 0.000 description 1
- 230000012495 positive regulation of renal sodium excretion Effects 0.000 description 1
- 238000004393 prognosis Methods 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
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- 238000011002 quantification Methods 0.000 description 1
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- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229940005573 sodium fumarate Drugs 0.000 description 1
- 235000019294 sodium fumarate Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 210000002820 sympathetic nervous system Anatomy 0.000 description 1
- WAMRXISPZIDVEO-UHFFFAOYSA-N tert-butyl n-[4-[tert-butyl(dimethyl)silyl]oxy-3-hydroxybutyl]-n-methylcarbamate Chemical compound CC(C)(C)OC(=O)N(C)CCC(O)CO[Si](C)(C)C(C)(C)C WAMRXISPZIDVEO-UHFFFAOYSA-N 0.000 description 1
- MSKMXVOFYNWASL-UHFFFAOYSA-N tert-butyl n-[4-[tert-butyl(dimethyl)silyl]oxy-3-hydroxybutyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCC(O)CO[Si](C)(C)C(C)(C)C MSKMXVOFYNWASL-UHFFFAOYSA-N 0.000 description 1
- MPHHYMDSSCDMPQ-UHFFFAOYSA-N tert-butyl n-[4-[tert-butyl(dimethyl)silyl]oxy-3-oxobutyl]-n-methylcarbamate Chemical compound CC(C)(C)OC(=O)N(C)CCC(=O)CO[Si](C)(C)C(C)(C)C MPHHYMDSSCDMPQ-UHFFFAOYSA-N 0.000 description 1
- PPZUZWSSIQZIGY-UHFFFAOYSA-N tert-butyl n-[4-[tert-butyl(dimethyl)silyl]oxy-3-oxobutyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCC(=O)CO[Si](C)(C)C(C)(C)C PPZUZWSSIQZIGY-UHFFFAOYSA-N 0.000 description 1
- JDDHLRUHQUWLHK-UHFFFAOYSA-N tert-butyl n-benzyl-n-[4-[tert-butyl(dimethyl)silyl]oxy-3-hydroxybutyl]carbamate Chemical compound CC(C)(C)[Si](C)(C)OCC(O)CCN(C(=O)OC(C)(C)C)CC1=CC=CC=C1 JDDHLRUHQUWLHK-UHFFFAOYSA-N 0.000 description 1
- HLAIZPWUFCAANQ-UHFFFAOYSA-N tert-butyl n-benzyl-n-[4-[tert-butyl(dimethyl)silyl]oxy-3-oxobutyl]carbamate Chemical compound CC(C)(C)[Si](C)(C)OCC(=O)CCN(C(=O)OC(C)(C)C)CC1=CC=CC=C1 HLAIZPWUFCAANQ-UHFFFAOYSA-N 0.000 description 1
- XBXCNNQPRYLIDE-UHFFFAOYSA-N tert-butylcarbamic acid Chemical compound CC(C)(C)NC(O)=O XBXCNNQPRYLIDE-UHFFFAOYSA-N 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero 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
- A61K31/4164—1,3-Diazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/409—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil having four such rings, e.g. porphine derivatives, bilirubin, biliverdine
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
- A61P9/12—Antihypertensives
-
- 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
- C07D233/66—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/84—Sulfur atoms
-
- 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
- C07D409/04—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 directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Epidemiology (AREA)
- Hospice & Palliative Care (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0223719 | 2002-10-11 | ||
| GB0223719A GB2393958A (en) | 2002-10-11 | 2002-10-11 | Peripherally-selective imidazole inhibitors of dopamine-beta-hydroxylase |
| GB0224306 | 2002-10-18 | ||
| GB0224306A GB2394223B (en) | 2002-10-11 | 2002-10-18 | Peripherally-selective inhibitors of dopamine-beta-hydroxylase and method of their preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2384118T3 true ES2384118T3 (es) | 2012-06-29 |
Family
ID=9945777
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES07076123T Expired - Lifetime ES2384118T3 (es) | 2002-10-11 | 2003-10-10 | Derivados de 3,4-dihidro-3-amino-2H-1-benzopirano y -benzotiopirano como inhibidores de la dopamina-beta-hidroxilasa y métodos para su preparación |
| ES07076125T Expired - Lifetime ES2364919T3 (es) | 2002-10-11 | 2003-10-10 | Cromano y tiocromano-3-il-1,3-dihidroimidazoles como inhibidores de la dopamina-beta-hidroxilasa y sus métodos de preparación. |
| ES07076122T Expired - Lifetime ES2361938T3 (es) | 2002-10-11 | 2003-10-10 | Hidroximetil-carbamoilalquil-cetonas protegidas por sililo como compuestos intermedios en la preparación de inhibidores de dopamina-beta-hidroxilasa. |
| ES03256420T Expired - Lifetime ES2309279T3 (es) | 2002-10-11 | 2003-10-10 | Derivados de imidazol y su uso como inhibidores perifericamente selectivos de la dopamina beta-hidroxilasa. |
| ES07076124T Expired - Lifetime ES2361939T3 (es) | 2002-10-11 | 2003-10-10 | Método de preparación de 3-(1,3-dihidroimidazol-2-tiona-1-il)-cromanos y tiocromanos como inhibidores de dopamina-beta-hidroxilasa. |
Family Applications After (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES07076125T Expired - Lifetime ES2364919T3 (es) | 2002-10-11 | 2003-10-10 | Cromano y tiocromano-3-il-1,3-dihidroimidazoles como inhibidores de la dopamina-beta-hidroxilasa y sus métodos de preparación. |
| ES07076122T Expired - Lifetime ES2361938T3 (es) | 2002-10-11 | 2003-10-10 | Hidroximetil-carbamoilalquil-cetonas protegidas por sililo como compuestos intermedios en la preparación de inhibidores de dopamina-beta-hidroxilasa. |
| ES03256420T Expired - Lifetime ES2309279T3 (es) | 2002-10-11 | 2003-10-10 | Derivados de imidazol y su uso como inhibidores perifericamente selectivos de la dopamina beta-hidroxilasa. |
| ES07076124T Expired - Lifetime ES2361939T3 (es) | 2002-10-11 | 2003-10-10 | Método de preparación de 3-(1,3-dihidroimidazol-2-tiona-1-il)-cromanos y tiocromanos como inhibidores de dopamina-beta-hidroxilasa. |
Country Status (11)
| Country | Link |
|---|---|
| KR (1) | KR101350741B1 (de) |
| CN (1) | CN100393715C (de) |
| AR (2) | AR041589A1 (de) |
| AT (5) | ATE403652T1 (de) |
| CY (2) | CY1108452T1 (de) |
| DE (4) | DE60336275D1 (de) |
| DK (2) | DK1908760T3 (de) |
| ES (5) | ES2384118T3 (de) |
| GB (2) | GB2393958A (de) |
| HK (1) | HK1116188A1 (de) |
| SI (2) | SI1908760T1 (de) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0708818D0 (en) * | 2007-05-08 | 2007-06-13 | Portela & Ca Sa | Compounds |
| KR101941467B1 (ko) * | 2010-12-22 | 2019-01-23 | 바이알 - 포르텔라 앤드 씨에이 에스에이 | 결정형 및 이들의 제조방법 |
| GB201316410D0 (en) | 2013-09-13 | 2013-10-30 | Bial Portela & Ca Sa | Processes for preparing peripherally-selective inhibitors of dopamine-?-hydroxylase and intermediates for use therein |
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| JP2581556B2 (ja) * | 1986-05-06 | 1997-02-12 | メレルダウファーマスーティカルズ インコーポレーテッド | 新規なドパミンベ−タヒドロキシラ−ゼ抑制剤 |
| US4868210A (en) | 1988-03-30 | 1989-09-19 | Warner-Lambert Company | Antihyperlipidemic and antiatherosclerotic compounds and compositions |
| PT757677E (pt) * | 1994-04-26 | 2003-11-28 | Syntex Llc | Derivados de benzociclohexilimidazoletiona |
-
2002
- 2002-10-11 GB GB0223719A patent/GB2393958A/en not_active Withdrawn
- 2002-10-18 GB GB0224306A patent/GB2394223B/en not_active Expired - Lifetime
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2003
- 2003-10-10 ES ES07076123T patent/ES2384118T3/es not_active Expired - Lifetime
- 2003-10-10 DE DE60336275T patent/DE60336275D1/de not_active Expired - Lifetime
- 2003-10-10 ES ES07076125T patent/ES2364919T3/es not_active Expired - Lifetime
- 2003-10-10 DE DE60336772T patent/DE60336772D1/de not_active Expired - Lifetime
- 2003-10-10 KR KR1020127005102A patent/KR101350741B1/ko active IP Right Grant
- 2003-10-10 SI SI200331986T patent/SI1908760T1/sl unknown
- 2003-10-10 AT AT03256420T patent/ATE403652T1/de active
- 2003-10-10 DK DK07076125.9T patent/DK1908760T3/da active
- 2003-10-10 AT AT07076125T patent/ATE505465T1/de active
- 2003-10-10 CN CNB2003801059426A patent/CN100393715C/zh not_active Expired - Fee Related
- 2003-10-10 DK DK03256420T patent/DK1408038T3/da active
- 2003-10-10 AT AT07076123T patent/ATE550335T1/de active
- 2003-10-10 DE DE60336276T patent/DE60336276D1/de not_active Expired - Lifetime
- 2003-10-10 ES ES07076122T patent/ES2361938T3/es not_active Expired - Lifetime
- 2003-10-10 AT AT07076124T patent/ATE500247T1/de not_active IP Right Cessation
- 2003-10-10 ES ES03256420T patent/ES2309279T3/es not_active Expired - Lifetime
- 2003-10-10 SI SI200331309T patent/SI1408038T1/sl unknown
- 2003-10-10 ES ES07076124T patent/ES2361939T3/es not_active Expired - Lifetime
- 2003-10-10 AT AT07076122T patent/ATE500248T1/de not_active IP Right Cessation
- 2003-10-10 AR ARP030103711A patent/AR041589A1/es active IP Right Grant
- 2003-10-10 DE DE60322642T patent/DE60322642D1/de not_active Expired - Lifetime
-
2008
- 2008-10-09 HK HK08111214.9A patent/HK1116188A1/xx not_active IP Right Cessation
- 2008-10-24 CY CY20081101204T patent/CY1108452T1/el unknown
-
2011
- 2011-07-01 CY CY20111100639T patent/CY1112457T1/el unknown
-
2014
- 2014-03-18 AR ARP140101283A patent/AR095674A2/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES2361938T3 (es) | 2011-06-24 |
| ES2361939T3 (es) | 2011-06-24 |
| KR20120038014A (ko) | 2012-04-20 |
| SI1408038T1 (sl) | 2008-10-31 |
| KR101350741B1 (ko) | 2014-01-10 |
| ATE550335T1 (de) | 2012-04-15 |
| ATE505465T1 (de) | 2011-04-15 |
| ATE500248T1 (de) | 2011-03-15 |
| DE60336276D1 (de) | 2011-04-14 |
| GB2393958A (en) | 2004-04-14 |
| DK1408038T3 (da) | 2008-11-24 |
| CN1726211A (zh) | 2006-01-25 |
| DE60336275D1 (de) | 2011-04-14 |
| GB2394223A (en) | 2004-04-21 |
| ATE403652T1 (de) | 2008-08-15 |
| GB0224306D0 (en) | 2002-11-27 |
| CY1108452T1 (el) | 2014-04-09 |
| AR041589A1 (es) | 2005-05-26 |
| ES2364919T3 (es) | 2011-09-16 |
| CY1112457T1 (el) | 2015-12-09 |
| ATE500247T1 (de) | 2011-03-15 |
| SI1908760T1 (sl) | 2011-05-31 |
| HK1116188A1 (en) | 2008-12-19 |
| GB2394223B (en) | 2007-05-16 |
| DE60322642D1 (de) | 2008-09-18 |
| ES2309279T3 (es) | 2008-12-16 |
| DE60336772D1 (de) | 2011-05-26 |
| AR095674A2 (es) | 2015-11-04 |
| CN100393715C (zh) | 2008-06-11 |
| GB0223719D0 (en) | 2002-11-20 |
| DK1908760T3 (da) | 2011-07-25 |
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