NO312133B1 - 4-amino-2-ureido-pyrimidin-5-karboksylsyreamider, fremgangsmåter for deres fremstilling, legemidler inneholdendedisse forbindelsene og deres anvendelse - Google Patents
4-amino-2-ureido-pyrimidin-5-karboksylsyreamider, fremgangsmåter for deres fremstilling, legemidler inneholdendedisse forbindelsene og deres anvendelse Download PDFInfo
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- NO312133B1 NO312133B1 NO19972942A NO972942A NO312133B1 NO 312133 B1 NO312133 B1 NO 312133B1 NO 19972942 A NO19972942 A NO 19972942A NO 972942 A NO972942 A NO 972942A NO 312133 B1 NO312133 B1 NO 312133B1
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- Norway
- Prior art keywords
- alkyl
- formula
- fluorine
- stands
- compound
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- 150000001875 compounds Chemical class 0.000 title claims description 79
- 238000000034 method Methods 0.000 title claims description 41
- 238000002360 preparation method Methods 0.000 title claims description 25
- SHGZREYDEWHPDB-UHFFFAOYSA-N 4-amino-2-(carbamoylamino)pyrimidine-5-carboxamide Chemical class NC(=O)NC1=NC=C(C(N)=O)C(N)=N1 SHGZREYDEWHPDB-UHFFFAOYSA-N 0.000 title claims description 3
- 239000003814 drug Substances 0.000 title description 7
- 229940079593 drug Drugs 0.000 title description 5
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 34
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 11
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 33
- 239000011737 fluorine Substances 0.000 claims description 33
- 239000000460 chlorine Substances 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
- -1 2,2,3,3,3-pentafluoropropyl Chemical group 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- PLYIXDXAACZULO-UHFFFAOYSA-N 2-(4,4-dimethyl-2-oxoimidazolidin-1-yl)-4-[(1-methylpyrrolidin-2-ylidene)amino]pyrimidine-5-carboxylic acid Chemical compound CN1CCCC1=NC1=NC(N2C(NC(C)(C)C2)=O)=NC=C1C(O)=O PLYIXDXAACZULO-UHFFFAOYSA-N 0.000 claims description 7
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- FPQVGDGSRVMNMR-JCTPKUEWSA-N [[(z)-(1-cyano-2-ethoxy-2-oxoethylidene)amino]oxy-(dimethylamino)methylidene]-dimethylazanium;tetrafluoroborate Chemical compound F[B-](F)(F)F.CCOC(=O)C(\C#N)=N/OC(N(C)C)=[N+](C)C FPQVGDGSRVMNMR-JCTPKUEWSA-N 0.000 claims description 4
- LRAFTRZPKUWQPO-UHFFFAOYSA-N ethyl 2-(4,4-dimethyl-2-oxoimidazolidin-1-yl)-4-[(1-methylpyrrolidin-2-ylidene)amino]pyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(N2C(NC(C)(C)C2)=O)N=C1N=C1CCCN1C LRAFTRZPKUWQPO-UHFFFAOYSA-N 0.000 claims description 4
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- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 3
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
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- LHWWETDBWVTKJO-UHFFFAOYSA-N et3n triethylamine Chemical compound CCN(CC)CC.CCN(CC)CC LHWWETDBWVTKJO-UHFFFAOYSA-N 0.000 description 1
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- 238000001704 evaporation Methods 0.000 description 1
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- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
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- 230000002503 metabolic effect Effects 0.000 description 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- 235000010981 methylcellulose Nutrition 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000010369 molecular cloning Methods 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- CALISYPJESQWEI-UHFFFAOYSA-N n-(2,2,3,3,4,4,4-heptafluorobutyl)-3-(trifluoromethyl)aniline Chemical compound FC(F)(F)C1=CC=CC(NCC(F)(F)C(F)(F)C(F)(F)F)=C1 CALISYPJESQWEI-UHFFFAOYSA-N 0.000 description 1
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 1
- VWBWQOUWDOULQN-UHFFFAOYSA-N nmp n-methylpyrrolidone Chemical compound CN1CCCC1=O.CN1CCCC1=O VWBWQOUWDOULQN-UHFFFAOYSA-N 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
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- 230000007170 pathology Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000007974 sodium acetate buffer Substances 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
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- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
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- 238000009736 wetting Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (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)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19625088A DE19625088A1 (de) | 1996-06-24 | 1996-06-24 | 4-Amino-2-ureido-pyrimidin-5-carbonsäureamide, Verfahren zu deren Herstellung, diese Verbindungen enthaltende Arzneimittel und deren Verwendung |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO972942D0 NO972942D0 (no) | 1997-06-23 |
| NO972942L NO972942L (no) | 1997-12-29 |
| NO312133B1 true NO312133B1 (no) | 2002-03-25 |
Family
ID=7797761
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19972942A NO312133B1 (no) | 1996-06-24 | 1997-06-23 | 4-amino-2-ureido-pyrimidin-5-karboksylsyreamider, fremgangsmåter for deres fremstilling, legemidler inneholdendedisse forbindelsene og deres anvendelse |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US5773447A (fr) |
| EP (1) | EP0816359B1 (fr) |
| JP (1) | JP4101905B2 (fr) |
| AT (1) | ATE281453T1 (fr) |
| CA (1) | CA2208611C (fr) |
| DE (2) | DE19625088A1 (fr) |
| DK (1) | DK0816359T3 (fr) |
| ES (1) | ES2230576T3 (fr) |
| MX (1) | MX9704621A (fr) |
| NO (1) | NO312133B1 (fr) |
| PT (1) | PT816359E (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19625089A1 (de) * | 1996-06-24 | 1998-01-02 | Hoechst Ag | 4-Amino-2-ureido-pyrimidin-5-carbonsäureamide, Verfahren zu deren Herstellung, diese Verbindungen enthaltende Arzneimittel und deren Verwendung |
| AU7683500A (en) | 1999-10-12 | 2001-04-23 | Takeda Chemical Industries Ltd. | Pyrimidine-5-carboxamide compounds, process for producing the same and use thereof |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2853220A1 (de) * | 1978-12-09 | 1980-07-03 | Hoechst Ag | Neue amino-pyrimidin-carbanilide, verfahren zu ihrer herstellung, diese verbindungen enthaltende arzneimittel und ihre verwendung |
| DE3522940A1 (de) * | 1985-06-27 | 1987-01-08 | Hoechst Ag | 4-amino-2-(imidazolidin-2-on-1-yl)-pyrimidin-5-carbonsaeure-(n-(3-trifluormethyl-phenyl)-amide) zur antithrombotischen prophylaxe und behandlung sowie ihre verwendung zur herstellung von antithrombotisch wirksamen arzneimitteln |
| ES2098570T3 (es) * | 1992-02-22 | 1997-05-01 | Hoechst Ag | Amidas de un acido 4-amino-2-ureido-pirimidina-5-carboxilico, procedimiento para su preparacion, medicamentos que contienen estos compuestos y su utilizacion. |
| DE59307402D1 (de) * | 1992-02-22 | 1997-10-30 | Hoechst Ag | Lösliche Salze von 4-Amino-2-(4,4-dimethyl-imidazolidin-2-on-1-yl)-pyrimidin-5 -carbonsäure- N-methyl-N-(3-trifluormethyl-phenyl)- amid, Verfahren zu ihrer Herstellung, ihre Verwendung als Arzneimittel und Ausgangsprodukte |
| DE19625089A1 (de) * | 1996-06-24 | 1998-01-02 | Hoechst Ag | 4-Amino-2-ureido-pyrimidin-5-carbonsäureamide, Verfahren zu deren Herstellung, diese Verbindungen enthaltende Arzneimittel und deren Verwendung |
-
1996
- 1996-06-24 DE DE19625088A patent/DE19625088A1/de not_active Withdrawn
-
1997
- 1997-06-12 ES ES97109548T patent/ES2230576T3/es not_active Expired - Lifetime
- 1997-06-12 PT PT97109548T patent/PT816359E/pt unknown
- 1997-06-12 EP EP97109548A patent/EP0816359B1/fr not_active Expired - Lifetime
- 1997-06-12 AT AT97109548T patent/ATE281453T1/de active
- 1997-06-12 DK DK97109548T patent/DK0816359T3/da active
- 1997-06-12 DE DE59712054T patent/DE59712054D1/de not_active Expired - Lifetime
- 1997-06-13 US US08/874,255 patent/US5773447A/en not_active Expired - Lifetime
- 1997-06-20 MX MX9704621A patent/MX9704621A/es not_active IP Right Cessation
- 1997-06-23 JP JP16581497A patent/JP4101905B2/ja not_active Expired - Fee Related
- 1997-06-23 CA CA002208611A patent/CA2208611C/fr not_active Expired - Fee Related
- 1997-06-23 NO NO19972942A patent/NO312133B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JPH1072462A (ja) | 1998-03-17 |
| NO972942D0 (no) | 1997-06-23 |
| NO972942L (no) | 1997-12-29 |
| EP0816359A1 (fr) | 1998-01-07 |
| PT816359E (pt) | 2005-02-28 |
| DE19625088A1 (de) | 1998-01-02 |
| CA2208611A1 (fr) | 1997-12-24 |
| ATE281453T1 (de) | 2004-11-15 |
| DE59712054D1 (de) | 2004-12-09 |
| DK0816359T3 (da) | 2005-03-14 |
| CA2208611C (fr) | 2006-10-03 |
| MX9704621A (es) | 1997-12-31 |
| EP0816359B1 (fr) | 2004-11-03 |
| US5773447A (en) | 1998-06-30 |
| ES2230576T3 (es) | 2005-05-01 |
| JP4101905B2 (ja) | 2008-06-18 |
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