NL8500564A - Pteridineverbindingen, werkwijze ter bereiding daarvan alsmede farmaceutische preparaten, die deze verbindingen bevatten. - Google Patents
Pteridineverbindingen, werkwijze ter bereiding daarvan alsmede farmaceutische preparaten, die deze verbindingen bevatten. Download PDFInfo
- Publication number
- NL8500564A NL8500564A NL8500564A NL8500564A NL8500564A NL 8500564 A NL8500564 A NL 8500564A NL 8500564 A NL8500564 A NL 8500564A NL 8500564 A NL8500564 A NL 8500564A NL 8500564 A NL8500564 A NL 8500564A
- Authority
- NL
- Netherlands
- Prior art keywords
- pteridine
- triamino
- addition salts
- phenyl
- acid addition
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 39
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical class N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 title claims description 9
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 6
- 239000002253 acid Substances 0.000 claims description 36
- 150000003839 salts Chemical class 0.000 claims description 34
- 239000013543 active substance Substances 0.000 claims description 33
- 238000002360 preparation method Methods 0.000 claims description 30
- -1 2-hydroxy-3-dimethylaminopropoxy Chemical group 0.000 claims description 26
- 230000001882 diuretic effect Effects 0.000 claims description 16
- 239000002934 diuretic Substances 0.000 claims description 14
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims description 9
- SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 claims description 8
- 229960003883 furosemide Drugs 0.000 claims description 8
- 229960001722 verapamil Drugs 0.000 claims description 8
- 230000003276 anti-hypertensive effect Effects 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- WDGZJFDDPCUVPF-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)phenyl]acetonitrile Chemical compound C1=CC(CC#N)=CC=C1OCC1OC1 WDGZJFDDPCUVPF-UHFFFAOYSA-N 0.000 claims description 6
- 230000003293 cardioprotective effect Effects 0.000 claims description 6
- 150000003195 pteridines Chemical class 0.000 claims description 6
- 230000000894 saliuretic effect Effects 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 4
- XLQQJSWJHHKLOK-UHFFFAOYSA-N 5-nitrosopyrimidine-2,4,6-triamine Chemical compound NC1=NC(N)=C(N=O)C(N)=N1 XLQQJSWJHHKLOK-UHFFFAOYSA-N 0.000 claims description 4
- JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 229960002003 hydrochlorothiazide Drugs 0.000 claims description 3
- JOMDGXNRGIOWDD-UHFFFAOYSA-N 1-(dibutylamino)-3-[4-(2,4,7-triaminopteridin-6-yl)phenoxy]propan-2-ol Chemical compound C1=CC(OCC(O)CN(CCCC)CCCC)=CC=C1C1=NC2=C(N)N=C(N)N=C2N=C1N JOMDGXNRGIOWDD-UHFFFAOYSA-N 0.000 claims description 2
- KWIAADKDDYGLJP-UHFFFAOYSA-N 1-(diethylamino)-3-[4-(2,4,7-triaminopteridin-6-yl)phenoxy]propan-2-ol Chemical compound C1=CC(OCC(O)CN(CC)CC)=CC=C1C1=NC2=C(N)N=C(N)N=C2N=C1N KWIAADKDDYGLJP-UHFFFAOYSA-N 0.000 claims description 2
- MGXSLGDTCJZZML-UHFFFAOYSA-N 1-piperidin-1-yl-3-[4-(2,4,7-triaminopteridin-6-yl)phenoxy]propan-2-ol Chemical compound NC1=NC2=NC(N)=NC(N)=C2N=C1C(C=C1)=CC=C1OCC(O)CN1CCCCC1 MGXSLGDTCJZZML-UHFFFAOYSA-N 0.000 claims description 2
- 229940127291 Calcium channel antagonist Drugs 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical class N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 claims description 2
- GCDKGCXABXOUMY-UHFFFAOYSA-N 1-amino-3-[4-(2,4,7-triaminopteridin-6-yl)phenoxy]propan-2-ol Chemical compound C1=CC(OCC(O)CN)=CC=C1C1=NC2=C(N)N=C(N)N=C2N=C1N GCDKGCXABXOUMY-UHFFFAOYSA-N 0.000 claims 2
- OWFYRPSFVAGYED-UHFFFAOYSA-N 1-(benzylamino)-3-[4-(2,4,7-triaminopteridin-6-yl)phenoxy]propan-2-ol Chemical compound NC1=NC2=NC(N)=NC(N)=C2N=C1C(C=C1)=CC=C1OCC(O)CNCC1=CC=CC=C1 OWFYRPSFVAGYED-UHFFFAOYSA-N 0.000 claims 1
- BFUPBHIAQRLABD-UHFFFAOYSA-N 1-(dipropylamino)-3-[4-(2,4,7-triaminopteridin-6-yl)phenoxy]propan-2-ol Chemical compound C1=CC(OCC(O)CN(CCC)CCC)=CC=C1C1=NC2=C(N)N=C(N)N=C2N=C1N BFUPBHIAQRLABD-UHFFFAOYSA-N 0.000 claims 1
- UTBHSGBXKZTPKZ-UHFFFAOYSA-N 1-(ethylamino)-3-[4-(2,4,7-triaminopteridin-6-yl)phenoxy]propan-2-ol Chemical compound C1=CC(OCC(O)CNCC)=CC=C1C1=NC2=C(N)N=C(N)N=C2N=C1N UTBHSGBXKZTPKZ-UHFFFAOYSA-N 0.000 claims 1
- KNUDFFQAXUGIEZ-UHFFFAOYSA-N 1-(methylamino)-3-[4-(2,4,7-triaminopteridin-6-yl)phenoxy]propan-2-ol Chemical compound C1=CC(OCC(O)CNC)=CC=C1C1=NC2=C(N)N=C(N)N=C2N=C1N KNUDFFQAXUGIEZ-UHFFFAOYSA-N 0.000 claims 1
- TWZNQMGDMLIUSB-UHFFFAOYSA-N 1-(propan-2-ylamino)-3-[4-(2,4,7-triaminopteridin-6-yl)phenoxy]propan-2-ol Chemical compound C1=CC(OCC(O)CNC(C)C)=CC=C1C1=NC2=C(N)N=C(N)N=C2N=C1N TWZNQMGDMLIUSB-UHFFFAOYSA-N 0.000 claims 1
- KXKCDDRESUFONP-UHFFFAOYSA-N 1-(propylamino)-3-[4-(2,4,7-triaminopteridin-6-yl)phenoxy]propan-2-ol Chemical compound C1=CC(OCC(O)CNCCC)=CC=C1C1=NC2=C(N)N=C(N)N=C2N=C1N KXKCDDRESUFONP-UHFFFAOYSA-N 0.000 claims 1
- IIKMUNDXWDKFFG-UHFFFAOYSA-N 1-[di(propan-2-yl)amino]-3-[4-(2,4,7-triaminopteridin-6-yl)phenoxy]propan-2-ol Chemical compound C1=CC(OCC(O)CN(C(C)C)C(C)C)=CC=C1C1=NC2=C(N)N=C(N)N=C2N=C1N IIKMUNDXWDKFFG-UHFFFAOYSA-N 0.000 claims 1
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- 239000002876 beta blocker Substances 0.000 claims 1
- 229940097320 beta blocking agent Drugs 0.000 claims 1
- 239000000480 calcium channel blocker Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
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- 239000000243 solution Substances 0.000 description 17
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
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- SMNOERSLNYGGOU-UHFFFAOYSA-N Mefruside Chemical compound C=1C=C(Cl)C(S(N)(=O)=O)=CC=1S(=O)(=O)N(C)CC1(C)CCCO1 SMNOERSLNYGGOU-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
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- 229910019142 PO4 Inorganic materials 0.000 description 1
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- 241000700159 Rattus Species 0.000 description 1
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- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Chemical class OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000005815 base catalysis Methods 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000007658 benzothiadiazines Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 150000003842 bromide salts Chemical class 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical class O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 230000002213 calciumantagonistic effect Effects 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229960001523 chlortalidone Drugs 0.000 description 1
- 230000007665 chronic toxicity Effects 0.000 description 1
- 231100000160 chronic toxicity Toxicity 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 229960005315 clorexolone Drugs 0.000 description 1
- 238000002648 combination therapy Methods 0.000 description 1
- 238000004590 computer program Methods 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- HSUGRBWQSSZJOP-RTWAWAEBSA-N diltiazem Chemical compound C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CCN(C)C)C2=CC=CC=C2S1 HSUGRBWQSSZJOP-RTWAWAEBSA-N 0.000 description 1
- 229960004166 diltiazem Drugs 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000035619 diuresis Effects 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000005048 flame photometry Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229960000457 gallopamil Drugs 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000000644 isotonic solution Substances 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229960004678 mefruside Drugs 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 150000007522 mineralic acids Chemical group 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229940097271 other diuretics in atc Drugs 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000011045 prefiltration Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 229960003712 propranolol Drugs 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical class O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229960000577 quinethazone Drugs 0.000 description 1
- AGMMTXLNIQSRCG-UHFFFAOYSA-N quinethazone Chemical compound NS(=O)(=O)C1=C(Cl)C=C2NC(CC)NC(=O)C2=C1 AGMMTXLNIQSRCG-UHFFFAOYSA-N 0.000 description 1
- 238000000611 regression analysis Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000007885 tablet disintegrant Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- 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
-
- 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
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D475/00—Heterocyclic compounds containing pteridine ring systems
- C07D475/06—Heterocyclic compounds containing pteridine ring systems with a nitrogen atom directly attached in position 4
- C07D475/08—Heterocyclic compounds containing pteridine ring systems with a nitrogen atom directly attached in position 4 with a nitrogen atom directly attached in position 2
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3407695 | 1984-03-02 | ||
| DE19843407695 DE3407695A1 (de) | 1984-03-02 | 1984-03-02 | Pteridinverbindungen mit pharmazeutischer wirksamkeit |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8500564A true NL8500564A (nl) | 1985-10-01 |
Family
ID=6229385
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8500564A NL8500564A (nl) | 1984-03-02 | 1985-02-28 | Pteridineverbindingen, werkwijze ter bereiding daarvan alsmede farmaceutische preparaten, die deze verbindingen bevatten. |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4910203A (es) |
| JP (1) | JPS60202885A (es) |
| AT (1) | AT392642B (es) |
| BE (1) | BE901850A (es) |
| CA (1) | CA1242441A (es) |
| CH (1) | CH667269A5 (es) |
| DD (1) | DD235871A5 (es) |
| DE (1) | DE3407695A1 (es) |
| ES (1) | ES8601695A1 (es) |
| FR (1) | FR2560598B1 (es) |
| GB (2) | GB2155923B (es) |
| HU (1) | HU198301B (es) |
| IT (1) | IT1183766B (es) |
| NL (1) | NL8500564A (es) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3913142A1 (de) * | 1989-04-21 | 1990-10-31 | Roehm Gmbh | Pharmazeutisch wirksame pteridinderivate |
| HU214331B (hu) * | 1992-06-17 | 1998-03-02 | Gyógyszerkutató Intézet Kft. | Eljárás piperazin- és homopiperazinszármazékok és ezeket tartalmazó gyógyszerkészítmények előállítására |
| CN106967069A (zh) * | 2017-03-22 | 2017-07-21 | 盐城市麦迪科化学品制造有限公司 | 一种氨苯蝶啶的制备方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3081230A (en) * | 1960-09-08 | 1963-03-12 | Smith Kline French Lab | Diuretic and antihypertensive triaminoarylpteridines |
| DE1593762A1 (de) * | 1967-02-06 | 1972-06-08 | Boehringer Sohn Ingelheim | Verfahren zur Herstellung von neuen substituierten 1-Phenoxy-2-hydroxy-3-alkylaminopropanen |
| CA945172A (en) * | 1969-02-21 | 1974-04-09 | Imperial Chemical Industries Limited | Alkanolamine derivatives |
| GB1521471A (en) * | 1974-06-05 | 1978-08-16 | Randall & Son Ltd J | Token-deposit locks |
| DE2503222A1 (de) * | 1975-01-27 | 1976-07-29 | Boehringer Sohn Ingelheim | Verfahren zur herstellung von 1-aryl- oxy-3-n-substituierten aminopropanderivaten |
| US4252809A (en) * | 1977-01-03 | 1981-02-24 | Rohm Pharma Gmbh | Substituted pteridine compounds and pharmaceutical compositions containing the same |
| FR2486082A2 (fr) * | 1977-01-03 | 1982-01-08 | Roehm Pharma Gmbh | Composes de la pteridine et leur application en tant que matieres therapeutiquement actives dans des preparations pharmaceutiques |
| DE2700073A1 (de) * | 1977-01-03 | 1978-07-13 | Roehm Pharma Gmbh | Pteridinverbindungen mit pharmazeutischer wirksamkeit |
| FR2387971A1 (fr) * | 1977-04-19 | 1978-11-17 | Delalande Sa | Nouvelles trimethoxy cinnamoyles piperazines, leur procede de preparation et leur application en therapeutique |
| FR2456738A2 (fr) * | 1978-04-10 | 1980-12-12 | Delalande Sa | Nouvelles cinnamoyles piperazines et homopiperazines, leur procede de preparation et leur application en therapeutique |
| US4285947A (en) * | 1980-01-18 | 1981-08-25 | Interx Research Corporation | Aldehyde adducts of triamterene |
| AT370722B (de) * | 1981-07-24 | 1983-04-25 | Gerot Pharmazeutika | Verfahren zur herstellung von 1-phenoxy-3-amino- 2-propanolen |
-
1984
- 1984-03-02 DE DE19843407695 patent/DE3407695A1/de not_active Withdrawn
-
1985
- 1985-01-30 AT AT254/85A patent/AT392642B/de not_active IP Right Cessation
- 1985-02-06 FR FR8501624A patent/FR2560598B1/fr not_active Expired
- 1985-02-21 CH CH809/85A patent/CH667269A5/de not_active IP Right Cessation
- 1985-02-25 ES ES540684A patent/ES8601695A1/es not_active Expired
- 1985-02-28 DD DD85273645A patent/DD235871A5/de not_active IP Right Cessation
- 1985-02-28 BE BE0/214588A patent/BE901850A/fr not_active IP Right Cessation
- 1985-02-28 NL NL8500564A patent/NL8500564A/nl not_active Application Discontinuation
- 1985-03-01 HU HU85767A patent/HU198301B/hu not_active IP Right Cessation
- 1985-03-01 CA CA000475633A patent/CA1242441A/en not_active Expired
- 1985-03-01 IT IT67216/85A patent/IT1183766B/it active
- 1985-03-01 GB GB08505277A patent/GB2155923B/en not_active Expired
- 1985-03-01 JP JP60038974A patent/JPS60202885A/ja active Pending
-
1987
- 1987-05-20 GB GB08711877A patent/GB2190084A/en not_active Withdrawn
-
1988
- 1988-04-20 US US07/185,319 patent/US4910203A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA1242441A (en) | 1988-09-27 |
| US4910203A (en) | 1990-03-20 |
| DD235871A5 (de) | 1986-05-21 |
| IT1183766B (it) | 1987-10-22 |
| IT8567216A1 (it) | 1986-09-01 |
| BE901850A (fr) | 1985-06-17 |
| HU198301B (en) | 1989-09-28 |
| GB8711877D0 (en) | 1987-06-24 |
| ATA25485A (de) | 1990-10-15 |
| FR2560598A1 (fr) | 1985-09-06 |
| IT8567216A0 (it) | 1985-03-01 |
| ES540684A0 (es) | 1985-12-01 |
| HUT37430A (en) | 1985-12-28 |
| JPS60202885A (ja) | 1985-10-14 |
| GB2190084A (en) | 1987-11-11 |
| GB8505277D0 (en) | 1985-04-03 |
| GB2155923A (en) | 1985-10-02 |
| DE3407695A1 (de) | 1985-09-12 |
| FR2560598B1 (fr) | 1988-03-18 |
| GB2155923B (en) | 1988-12-14 |
| AT392642B (de) | 1991-05-10 |
| CH667269A5 (de) | 1988-09-30 |
| ES8601695A1 (es) | 1985-12-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BA | A request for search or an international-type search has been filed | ||
| BB | A search report has been drawn up | ||
| BV | The patent application has lapsed |