CA2387123A1 - Utilisation de thienopyrimidines - Google Patents
Utilisation de thienopyrimidines Download PDFInfo
- Publication number
- CA2387123A1 CA2387123A1 CA002387123A CA2387123A CA2387123A1 CA 2387123 A1 CA2387123 A1 CA 2387123A1 CA 002387123 A CA002387123 A CA 002387123A CA 2387123 A CA2387123 A CA 2387123A CA 2387123 A1 CA2387123 A1 CA 2387123A1
- Authority
- CA
- Canada
- Prior art keywords
- pyrimidin
- acid
- thieno
- benzo
- chloro
- 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.)
- Abandoned
Links
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 239000003814 drug Substances 0.000 claims abstract description 13
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- 206010002383 Angina Pectoris Diseases 0.000 claims abstract description 8
- 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 8
- 206010007559 Cardiac failure congestive Diseases 0.000 claims abstract description 8
- 206010016654 Fibrosis Diseases 0.000 claims abstract description 8
- 208000010412 Glaucoma Diseases 0.000 claims abstract description 8
- 206010019280 Heart failures Diseases 0.000 claims abstract description 8
- 206010020772 Hypertension Diseases 0.000 claims abstract description 8
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 8
- 208000018262 Peripheral vascular disease Diseases 0.000 claims abstract description 8
- 208000001647 Renal Insufficiency Diseases 0.000 claims abstract description 8
- 206010039085 Rhinitis allergic Diseases 0.000 claims abstract description 8
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- 201000009961 allergic asthma Diseases 0.000 claims abstract description 8
- 201000010105 allergic rhinitis Diseases 0.000 claims abstract description 8
- 208000006673 asthma Diseases 0.000 claims abstract description 8
- 206010006451 bronchitis Diseases 0.000 claims abstract description 8
- 208000023819 chronic asthma Diseases 0.000 claims abstract description 8
- 230000007882 cirrhosis Effects 0.000 claims abstract description 8
- 208000019425 cirrhosis of liver Diseases 0.000 claims abstract description 8
- 208000002551 irritable bowel syndrome Diseases 0.000 claims abstract description 8
- 201000006370 kidney failure Diseases 0.000 claims abstract description 8
- 210000004185 liver Anatomy 0.000 claims abstract description 8
- 239000012453 solvate Substances 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 35
- -1 COOA Chemical group 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- 230000000747 cardiac effect Effects 0.000 claims description 7
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 230000002685 pulmonary effect Effects 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- YKNCNWFUQFZYCW-UHFFFAOYSA-N 3-[4-[(3-chloro-4-methoxyphenyl)methylamino]-[1]benzothiolo[2,3-d]pyrimidin-2-yl]propanoic acid Chemical compound C1=C(Cl)C(OC)=CC=C1CNC1=NC(CCC(O)=O)=NC2=C1C1=CC=CC=C1S2 YKNCNWFUQFZYCW-UHFFFAOYSA-N 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- XRNQSOGCDORRGQ-UHFFFAOYSA-N 2-[4-[4-(1,3-benzodioxol-5-ylmethylamino)-[1]benzothiolo[2,3-d]pyrimidin-2-yl]phenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1C1=NC(NCC=2C=C3OCOC3=CC=2)=C2C3=CC=CC=C3SC2=N1 XRNQSOGCDORRGQ-UHFFFAOYSA-N 0.000 claims description 2
- KBWPAGXDPUXKIT-UHFFFAOYSA-N 2-[4-[4-[(3-chloro-4-methoxyphenyl)methylamino]-[1]benzothiolo[2,3-d]pyrimidin-2-yl]cyclohexylidene]acetic acid Chemical compound C1=C(Cl)C(OC)=CC=C1CNC1=NC(C2CCC(CC2)=CC(O)=O)=NC2=C1C1=CC=CC=C1S2 KBWPAGXDPUXKIT-UHFFFAOYSA-N 0.000 claims description 2
- AFUYBPXWBNFSNJ-UHFFFAOYSA-N 4-[4-(1,3-benzodioxol-5-ylmethylamino)-[1]benzothiolo[2,3-d]pyrimidin-2-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=NC(NCC=2C=C3OCOC3=CC=2)=C2C3=CC=CC=C3SC2=N1 AFUYBPXWBNFSNJ-UHFFFAOYSA-N 0.000 claims description 2
- IUQLCYAQFPLIOX-UHFFFAOYSA-N 4-[4-(1,3-benzodioxol-5-ylmethylamino)-[1]benzothiolo[2,3-d]pyrimidin-2-yl]butanoic acid Chemical compound C1=CC=C2C3=C(NCC=4C=C5OCOC5=CC=4)N=C(CCCC(=O)O)N=C3SC2=C1 IUQLCYAQFPLIOX-UHFFFAOYSA-N 0.000 claims description 2
- CYJGZDCCKXCNOF-UHFFFAOYSA-N 4-[4-(1,3-benzodioxol-5-ylmethylamino)-[1]benzothiolo[2,3-d]pyrimidin-2-yl]cyclohexane-1-carboxylic acid Chemical compound C1CC(C(=O)O)CCC1C1=NC(NCC=2C=C3OCOC3=CC=2)=C2C3=CC=CC=C3SC2=N1 CYJGZDCCKXCNOF-UHFFFAOYSA-N 0.000 claims description 2
- VXCPPJWBHMZOCM-UHFFFAOYSA-N 5-[4-[(3-chloro-4-methoxyphenyl)methylamino]-[1]benzothiolo[2,3-d]pyrimidin-2-yl]pentanoic acid Chemical compound C1=C(Cl)C(OC)=CC=C1CNC1=NC(CCCCC(O)=O)=NC2=C1C1=CC=CC=C1S2 VXCPPJWBHMZOCM-UHFFFAOYSA-N 0.000 claims description 2
- QVHPHQZZUULWAS-UHFFFAOYSA-N 7-[4-(1,3-benzodioxol-5-ylmethylamino)-[1]benzothiolo[2,3-d]pyrimidin-2-yl]heptanoic acid Chemical compound C1=CC=C2C3=C(NCC=4C=C5OCOC5=CC=4)N=C(CCCCCCC(=O)O)N=C3SC2=C1 QVHPHQZZUULWAS-UHFFFAOYSA-N 0.000 claims description 2
- OGMKXSIWCDVZCH-UHFFFAOYSA-N 7-[4-[(3-chloro-4-methoxyphenyl)methylamino]-[1]benzothiolo[2,3-d]pyrimidin-2-yl]heptanoic acid Chemical compound C1=C(Cl)C(OC)=CC=C1CNC1=NC(CCCCCCC(O)=O)=NC2=C1C1=CC=CC=C1S2 OGMKXSIWCDVZCH-UHFFFAOYSA-N 0.000 claims description 2
- FZGGYQRBEGBYPI-UHFFFAOYSA-N ClC=1C=C(CNC=2C3=C(N=C(N=2)C2CCC(CC2)=C2C(CCCC2)C(=O)O)SC2=C3C=CC=C2)C=CC=1OC Chemical compound ClC=1C=C(CNC=2C3=C(N=C(N=2)C2CCC(CC2)=C2C(CCCC2)C(=O)O)SC2=C3C=CC=C2)C=CC=1OC FZGGYQRBEGBYPI-UHFFFAOYSA-N 0.000 claims 1
- 208000002815 pulmonary hypertension Diseases 0.000 abstract 1
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- 150000002169 ethanolamines Chemical class 0.000 description 8
- ZILSBZLQGRBMOR-UHFFFAOYSA-N 1,3-benzodioxol-5-ylmethanamine Chemical compound NCC1=CC=C2OCOC2=C1 ZILSBZLQGRBMOR-UHFFFAOYSA-N 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 5
- ZOOGRGPOEVQQDX-KHLHZJAASA-N cyclic guanosine monophosphate Chemical compound C([C@H]1O2)O[P@](O)(=O)O[C@@H]1[C@H](O)[C@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-KHLHZJAASA-N 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000010626 work up procedure Methods 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
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- 239000012442 inert solvent Substances 0.000 description 4
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- 239000007924 injection Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000012154 double-distilled water Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- SQWORADQQHMZRJ-UHFFFAOYSA-N methyl 3-(4-chloro-[1]benzothiolo[2,3-d]pyrimidin-2-yl)propanoate Chemical compound C1=CC=C2C3=C(Cl)N=C(CCC(=O)OC)N=C3SC2=C1 SQWORADQQHMZRJ-UHFFFAOYSA-N 0.000 description 3
- FKHOQCZVABWRTP-UHFFFAOYSA-N methyl 4-(4-chloro-[1]benzothiolo[2,3-d]pyrimidin-2-yl)butanoate Chemical compound C1=CC=C2C3=C(Cl)N=C(CCCC(=O)OC)N=C3SC2=C1 FKHOQCZVABWRTP-UHFFFAOYSA-N 0.000 description 3
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- AFJBPSJWEMASMS-UHFFFAOYSA-N methyl 2-[4-(4-chloro-[1]benzothiolo[2,3-d]pyrimidin-2-yl)cyclohexyl]acetate Chemical compound C1CC(CC(=O)OC)CCC1C1=NC(Cl)=C2C3=CC=CC=C3SC2=N1 AFJBPSJWEMASMS-UHFFFAOYSA-N 0.000 description 2
- BOTCDYGKZXRYSH-UHFFFAOYSA-N methyl 3-[4-[(3-chloro-4-methoxyphenyl)methylamino]-[1]benzothiolo[2,3-d]pyrimidin-2-yl]propanoate Chemical compound S1C2=CC=CC=C2C=2C1=NC(CCC(=O)OC)=NC=2NCC1=CC=C(OC)C(Cl)=C1 BOTCDYGKZXRYSH-UHFFFAOYSA-N 0.000 description 2
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- 150000002826 nitrites Chemical class 0.000 description 2
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- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 2
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- 238000007363 ring formation reaction Methods 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
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000008347 soybean phospholipid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 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
- 150000003577 thiophenes Chemical class 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 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
- 229960002622 triacetin Drugs 0.000 description 1
- 229960002415 trichloroethylene Drugs 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- 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
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious 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
- A61P9/10—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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (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)
- Pulmonology (AREA)
- Urology & Nephrology (AREA)
- Epidemiology (AREA)
- Ophthalmology & Optometry (AREA)
- Immunology (AREA)
- Vascular Medicine (AREA)
- Toxicology (AREA)
- Gastroenterology & Hepatology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Hospice & Palliative Care (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Thiénopyrimidines de formule (I), ainsi que des sels et/ou solvates acceptables sur le plan physiologique desdites substances. Dans la formule (I), R?1¿, R?2¿ et X possèdent la signification figurant dans la revendication 1. Lesdites substances sont utilisées pour préparer un médicament destiné à traiter l'angine de poitrine, l'hypertension artérielle, l'hypertension pulmonaire, l'insuffisance cardiaque congestive, l'athérosclérose, la réduction du passage dans les vaisseaux cardiaques, les maladies vasculaires périphériques, l'accident vasculaire cérébral, la bronchite, l'asthme allergique, l'asthme chronique, la rhinite allergique, le glaucome, le syndrome du colon irritable, les tumeurs, l'insuffisance rénale, la cirrhose du foie et l'impuissance féminine.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19943815A DE19943815A1 (de) | 1999-09-14 | 1999-09-14 | Verwendung von Thienopyrimidinen |
| DE19943815.3 | 1999-09-14 | ||
| PCT/EP2000/008258 WO2001019369A1 (fr) | 1999-09-14 | 2000-08-24 | Utilisation de thiénopyrimidines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2387123A1 true CA2387123A1 (fr) | 2001-03-22 |
Family
ID=7921854
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002387123A Abandoned CA2387123A1 (fr) | 1999-09-14 | 2000-08-24 | Utilisation de thienopyrimidines |
Country Status (18)
| Country | Link |
|---|---|
| EP (1) | EP1212062A1 (fr) |
| JP (1) | JP2003509370A (fr) |
| KR (1) | KR20020026011A (fr) |
| CN (1) | CN1377271A (fr) |
| AR (1) | AR025645A1 (fr) |
| AU (1) | AU6703200A (fr) |
| BR (1) | BR0013957A (fr) |
| CA (1) | CA2387123A1 (fr) |
| CZ (1) | CZ2002818A3 (fr) |
| DE (1) | DE19943815A1 (fr) |
| HU (1) | HUP0202614A3 (fr) |
| MX (1) | MXPA02002746A (fr) |
| NO (1) | NO20021234D0 (fr) |
| PL (1) | PL353343A1 (fr) |
| RU (1) | RU2002107441A (fr) |
| SK (1) | SK3322002A3 (fr) |
| WO (1) | WO2001019369A1 (fr) |
| ZA (1) | ZA200202868B (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1347762A2 (fr) * | 2000-12-19 | 2003-10-01 | MERCK PATENT GmbH | Formulation pharmaceutique contenant des thienopyrimidines et des antithrombotiques, des inhibiteurs calciques, des prostaglandines ou des derives de prostaglandine (2) |
| DE10135815A1 (de) * | 2001-07-23 | 2003-02-06 | Bayer Ag | Verwendung von 2-Alkoxyphenyl-substituierten Imidazotriazinonen |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5869486A (en) * | 1995-02-24 | 1999-02-09 | Ono Pharmaceutical Co., Ltd. | Fused pyrimidines and pyriazines as pharmaceutical compounds |
| HU228446B1 (en) * | 1996-04-12 | 2013-03-28 | Warner Lambert Co | Kinazoline derivatives as irreversible inhibitors of protein-kinase, pharmaceutical compositions containing these compounds and use thereof |
| DE19644228A1 (de) * | 1996-10-24 | 1998-04-30 | Merck Patent Gmbh | Thienopyrimidine |
| DE19819023A1 (de) * | 1998-04-29 | 1999-11-04 | Merck Patent Gmbh | Thienopyrimidine |
| US5948911A (en) * | 1998-11-20 | 1999-09-07 | Cell Pathways, Inc. | Method for inhibiting neoplastic cells and related conditions by exposure to thienopyrimidine derivatives |
| WO2000059912A1 (fr) * | 1999-03-30 | 2000-10-12 | Nippon Soda Co., Ltd. | Composes de thienopyrimidine et leurs sels, et procede de preparation desdits composes et sels |
-
1999
- 1999-09-14 DE DE19943815A patent/DE19943815A1/de not_active Withdrawn
-
2000
- 2000-08-24 CN CN00813731A patent/CN1377271A/zh active Pending
- 2000-08-24 SK SK332-2002A patent/SK3322002A3/sk unknown
- 2000-08-24 EP EP00954650A patent/EP1212062A1/fr not_active Withdrawn
- 2000-08-24 MX MXPA02002746A patent/MXPA02002746A/es not_active Application Discontinuation
- 2000-08-24 JP JP2001523002A patent/JP2003509370A/ja active Pending
- 2000-08-24 CZ CZ2002818A patent/CZ2002818A3/cs unknown
- 2000-08-24 HU HU0202614A patent/HUP0202614A3/hu unknown
- 2000-08-24 BR BR0013957-2A patent/BR0013957A/pt not_active IP Right Cessation
- 2000-08-24 WO PCT/EP2000/008258 patent/WO2001019369A1/fr not_active Ceased
- 2000-08-24 CA CA002387123A patent/CA2387123A1/fr not_active Abandoned
- 2000-08-24 RU RU2002107441/14A patent/RU2002107441A/ru not_active Application Discontinuation
- 2000-08-24 PL PL00353343A patent/PL353343A1/xx unknown
- 2000-08-24 AU AU67032/00A patent/AU6703200A/en not_active Abandoned
- 2000-08-24 KR KR1020027003303A patent/KR20020026011A/ko not_active Withdrawn
- 2000-09-13 AR ARP000104796A patent/AR025645A1/es not_active Application Discontinuation
-
2002
- 2002-03-13 NO NO20021234A patent/NO20021234D0/no not_active Application Discontinuation
- 2002-04-11 ZA ZA200202868A patent/ZA200202868B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR0013957A (pt) | 2002-05-21 |
| CZ2002818A3 (cs) | 2002-06-12 |
| WO2001019369A1 (fr) | 2001-03-22 |
| CN1377271A (zh) | 2002-10-30 |
| HUP0202614A3 (en) | 2004-11-29 |
| ZA200202868B (en) | 2003-11-26 |
| SK3322002A3 (en) | 2002-07-02 |
| PL353343A1 (en) | 2003-11-17 |
| DE19943815A1 (de) | 2001-03-15 |
| AR025645A1 (es) | 2002-12-04 |
| MXPA02002746A (es) | 2002-10-23 |
| JP2003509370A (ja) | 2003-03-11 |
| NO20021234L (no) | 2002-03-13 |
| AU6703200A (en) | 2001-04-17 |
| HUP0202614A2 (hu) | 2002-12-28 |
| RU2002107441A (ru) | 2003-11-20 |
| EP1212062A1 (fr) | 2002-06-12 |
| NO20021234D0 (no) | 2002-03-13 |
| KR20020026011A (ko) | 2002-04-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |