DE2512673A1 - 7-(hydroxyphenyl)pyrido eckige klammer auf 3,4-d eckige klammer zu pyridazine und verfahren zu ihrer herstellung - Google Patents
7-(hydroxyphenyl)pyrido eckige klammer auf 3,4-d eckige klammer zu pyridazine und verfahren zu ihrer herstellungInfo
- Publication number
- DE2512673A1 DE2512673A1 DE19752512673 DE2512673A DE2512673A1 DE 2512673 A1 DE2512673 A1 DE 2512673A1 DE 19752512673 DE19752512673 DE 19752512673 DE 2512673 A DE2512673 A DE 2512673A DE 2512673 A1 DE2512673 A1 DE 2512673A1
- Authority
- DE
- Germany
- Prior art keywords
- hydroxyphenyl
- pyrido
- pyridazine
- group
- benzyloxyphenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 43
- -1 HYDROXYPHENYL Chemical class 0.000 title claims description 38
- 230000008569 process Effects 0.000 title claims description 29
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 28
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 238000003776 cleavage reaction Methods 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 230000007017 scission Effects 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000004892 pyridazines Chemical class 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- 238000002844 melting Methods 0.000 description 22
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- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 19
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 11
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
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- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 239000007868 Raney catalyst Substances 0.000 description 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 230000029142 excretion Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- BKRPJAZBATYPMW-UHFFFAOYSA-N 6-(4-hydroxyphenyl)-2-phenylpyrrolo[3,4-c]pyridine-1,3-dione Chemical compound C1=CC(O)=CC=C1C(N=C1)=CC2=C1C(=O)N(C=1C=CC=CC=1)C2=O BKRPJAZBATYPMW-UHFFFAOYSA-N 0.000 description 2
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- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
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- TXHIDIHEXDFONW-UHFFFAOYSA-N benzene;propan-2-one Chemical compound CC(C)=O.C1=CC=CC=C1 TXHIDIHEXDFONW-UHFFFAOYSA-N 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
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- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
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- 239000003054 catalyst Substances 0.000 description 2
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- 230000000694 effects Effects 0.000 description 2
- RCZMENSGPGPIQI-UHFFFAOYSA-N ethyl 5-cyano-2-(4-phenylmethoxyphenyl)pyridine-4-carboxylate Chemical compound C1=C(C#N)C(C(=O)OCC)=CC(C=2C=CC(OCC=3C=CC=CC=3)=CC=2)=N1 RCZMENSGPGPIQI-UHFFFAOYSA-N 0.000 description 2
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- 239000011259 mixed solution Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 231100000989 no adverse effect Toxicity 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- KNPBKKLNMDSNPI-UHFFFAOYSA-N pyridazin-1-ium 2,2,2-trifluoroacetate Chemical compound C1=CN=NC=C1.OC(=O)C(F)(F)F KNPBKKLNMDSNPI-UHFFFAOYSA-N 0.000 description 1
- 229940070891 pyridium Drugs 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 150000003463 sulfur Chemical class 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 229960001288 triamterene Drugs 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- 208000009852 uremia Diseases 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
- C07D213/85—Nitriles in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Hematology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP49033679A JPS5811874B2 (ja) | 1974-03-25 | 1974-03-25 | ピリド （３，４−ｄ） ピリダジンルイノ セイゾウホウ |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2512673A1 true DE2512673A1 (de) | 1975-10-02 |
Family
ID=12393114
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752512673 Withdrawn DE2512673A1 (de) | 1974-03-25 | 1975-03-21 | 7-(hydroxyphenyl)pyrido eckige klammer auf 3,4-d eckige klammer zu pyridazine und verfahren zu ihrer herstellung |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4005201A (en, 2012) |
| JP (1) | JPS5811874B2 (en, 2012) |
| AT (1) | AT342064B (en, 2012) |
| BE (1) | BE827103A (en, 2012) |
| CA (1) | CA1044234A (en, 2012) |
| CH (1) | CH597229A5 (en, 2012) |
| DE (1) | DE2512673A1 (en, 2012) |
| DK (1) | DK134554B (en, 2012) |
| ES (1) | ES435955A1 (en, 2012) |
| FR (1) | FR2265384B1 (en, 2012) |
| GB (1) | GB1503032A (en, 2012) |
| HU (1) | HU169631B (en, 2012) |
| NL (1) | NL7503289A (en, 2012) |
| NO (1) | NO141852C (en, 2012) |
| SE (1) | SE419987B (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6858602B2 (en) | 2001-06-12 | 2005-02-22 | Wellstat Therapeutics Corporation | Compounds for the treatment of metabolic disorders |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2056142A1 (en) * | 1990-11-27 | 1992-05-28 | Hirotomo Masuya | Pyridopyridazine compounds and their use |
| DE19500760A1 (de) * | 1995-01-13 | 1996-07-18 | Basf Ag | Substituierte 2-Phenylpyridine |
| US8722668B2 (en) * | 1998-12-23 | 2014-05-13 | Daryl W. Hochman | Methods and compositions for the treatment of neuropathic pain and neuropsychiatric disorders |
| US8008283B2 (en) * | 1998-12-23 | 2011-08-30 | Neurotherapeutics Pharma, Inc. | Methods and compositions for the treatment of neuropsychiatric disorders |
| EP1951702A2 (en) * | 2005-10-17 | 2008-08-06 | NeuroTherapeutics Pharma, Inc. | Diuretic-like compound analogs useful for regulation of central nervous system disorders |
| CN108484494B (zh) * | 2018-06-15 | 2021-07-30 | 沈阳药科大学 | 2-氧代-1,2-二氢吡啶-4-甲酸类化合物 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE793345A (fr) * | 1971-12-28 | 1973-06-27 | Takeda Chemical Industries Ltd | Derives de pyridopyridazine |
-
1974
- 1974-03-25 JP JP49033679A patent/JPS5811874B2/ja not_active Expired
-
1975
- 1975-03-19 NO NO750939A patent/NO141852C/no unknown
- 1975-03-19 NL NL7503289A patent/NL7503289A/xx not_active Application Discontinuation
- 1975-03-20 AT AT214775A patent/AT342064B/de not_active IP Right Cessation
- 1975-03-21 DE DE19752512673 patent/DE2512673A1/de not_active Withdrawn
- 1975-03-21 CH CH369075A patent/CH597229A5/xx not_active IP Right Cessation
- 1975-03-24 DK DK123975AA patent/DK134554B/da unknown
- 1975-03-24 SE SE7503391A patent/SE419987B/xx unknown
- 1975-03-24 CA CA222,886A patent/CA1044234A/en not_active Expired
- 1975-03-24 BE BE154691A patent/BE827103A/xx unknown
- 1975-03-24 HU HUTA1349A patent/HU169631B/hu unknown
- 1975-03-24 FR FR7509113A patent/FR2265384B1/fr not_active Expired
- 1975-03-24 ES ES0435955A patent/ES435955A1/es not_active Expired
- 1975-03-25 US US05/562,034 patent/US4005201A/en not_active Expired - Lifetime
- 1975-03-25 GB GB12366/75A patent/GB1503032A/en not_active Expired
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6858602B2 (en) | 2001-06-12 | 2005-02-22 | Wellstat Therapeutics Corporation | Compounds for the treatment of metabolic disorders |
| US6916848B2 (en) | 2001-06-12 | 2005-07-12 | Wellstat Therapeutics Corporation | Compounds for the treatment of metabolic disorders |
| US6924314B2 (en) | 2001-06-12 | 2005-08-02 | Wellstat Therapeutics Corporation | Compounds for the treatment of metabolic disorders |
| US6946491B2 (en) | 2001-06-12 | 2005-09-20 | Wellstat Therapeutics Corporation | Compounds for the treatment of metabolic disorders |
| US7012071B2 (en) | 2001-06-12 | 2006-03-14 | Wellstat Therapeutics Corporation | Compounds for the treatment of metabolic disorders |
| US7041659B2 (en) | 2001-06-12 | 2006-05-09 | Wellstat Therapeutics Corporation | Compounds for the treatment of metabolic disorders |
| US7045541B2 (en) | 2001-06-12 | 2006-05-16 | Wellstat Therapeutics Corporation | Compounds for the treatment of metabolic disorders |
| US7101910B2 (en) | 2001-06-12 | 2006-09-05 | Wellstat Therapeutics Corporation | Compounds for the treatment of metabolic disorders |
| US7329782B2 (en) | 2001-06-12 | 2008-02-12 | Wellstat Therapeutics Corporation | Compounds for the treatment of metabolic disorders |
| US7547802B2 (en) | 2001-06-12 | 2009-06-16 | Wellstat Therapeutics Corporation | Compounds for the treatment of metabolic disorders |
| US7863475B2 (en) | 2001-06-12 | 2011-01-04 | Wellstat Therapeutics Corporation | Compounds for the treatment of metabolic disorders |
| US8487000B2 (en) | 2001-06-12 | 2013-07-16 | Wellstat Therapertics Corporation | Compound for the treatment of metabolic disorders |
| US8552062B2 (en) | 2001-06-12 | 2013-10-08 | Wellstat Therapeutics Corporation | Methods for the treatment of metabolic disorders such as diabetes |
| US8604083B2 (en) | 2001-06-12 | 2013-12-10 | Wellstat Therapeutics Corporation | Method for the treatment of metabolic disorders |
Also Published As
| Publication number | Publication date |
|---|---|
| BE827103A (fr) | 1975-09-24 |
| FR2265384B1 (en, 2012) | 1980-01-18 |
| JPS50129594A (en, 2012) | 1975-10-13 |
| NL7503289A (nl) | 1975-09-29 |
| SE7503391L (en, 2012) | 1975-09-26 |
| HU169631B (en, 2012) | 1976-12-28 |
| NO141852C (no) | 1980-06-04 |
| NO141852B (no) | 1980-02-11 |
| NO750939L (en, 2012) | 1975-09-26 |
| US4005201A (en) | 1977-01-25 |
| DK134554B (da) | 1976-11-29 |
| SE419987B (sv) | 1981-09-07 |
| CH597229A5 (en, 2012) | 1978-03-31 |
| AT342064B (de) | 1978-03-10 |
| DK123975A (en, 2012) | 1975-09-26 |
| ATA214775A (de) | 1977-07-15 |
| FR2265384A1 (en, 2012) | 1975-10-24 |
| AU7944875A (en) | 1976-09-30 |
| ES435955A1 (es) | 1977-01-01 |
| DK134554C (en, 2012) | 1977-05-02 |
| CA1044234A (en) | 1978-12-12 |
| GB1503032A (en) | 1978-03-08 |
| JPS5811874B2 (ja) | 1983-03-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |