IE49469B1 - Substituted quinazolines - Google Patents
Substituted quinazolinesInfo
- Publication number
- IE49469B1 IE49469B1 IE2364/79A IE236479A IE49469B1 IE 49469 B1 IE49469 B1 IE 49469B1 IE 2364/79 A IE2364/79 A IE 2364/79A IE 236479 A IE236479 A IE 236479A IE 49469 B1 IE49469 B1 IE 49469B1
- Authority
- IE
- Ireland
- Prior art keywords
- compound
- dimethoxy
- quinazolinone
- reaction
- hours
- Prior art date
Links
- 150000003246 quinazolines Chemical class 0.000 title abstract description 5
- 239000002253 acid Substances 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000003118 aryl group Chemical group 0.000 claims abstract description 8
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims abstract description 6
- 125000003368 amide group Chemical group 0.000 claims abstract description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims abstract description 4
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- 239000011541 reaction mixture Substances 0.000 claims description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 11
- -1 COO loweralkyl Chemical group 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 10
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims description 8
- 239000005695 Ammonium acetate Substances 0.000 claims description 8
- 235000019257 ammonium acetate Nutrition 0.000 claims description 8
- 229940043376 ammonium acetate Drugs 0.000 claims description 8
- 239000004202 carbamide Substances 0.000 claims description 7
- JICRAAJVFXLBBI-UHFFFAOYSA-N 4-decyl-6,7-dimethoxy-3H-quinazolin-2-one Chemical compound C(CCCCCCCCC)C1=NC(NC2=CC(=C(C=C12)OC)OC)=O JICRAAJVFXLBBI-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- UQNNDXNLUAXSQI-UHFFFAOYSA-N n-[(3,4-dimethoxyphenyl)carbamoyl]heptanamide Chemical compound CCCCCCC(=O)NC(=O)NC1=CC=C(OC)C(OC)=C1 UQNNDXNLUAXSQI-UHFFFAOYSA-N 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- BGAHFOVLISWDQZ-UHFFFAOYSA-N 4-hexyl-6,7-dimethoxy-3H-quinazolin-2-one Chemical compound COC=1C=C2C(=NC(NC2=CC1OC)=O)CCCCCC BGAHFOVLISWDQZ-UHFFFAOYSA-N 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 4
- JNEKNSDJLZOWFV-UHFFFAOYSA-N N-[(3,4-dimethoxyphenyl)carbamoyl]heptadecanamide Chemical compound COC=1C=C(C=CC1OC)NC(=O)NC(CCCCCCCCCCCCCCCC)=O JNEKNSDJLZOWFV-UHFFFAOYSA-N 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 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 1
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- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 abstract description 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 abstract description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 abstract 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
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- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 1
- 239000007787 solid Substances 0.000 description 40
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- 239000000243 solution Substances 0.000 description 26
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- 239000000203 mixture Substances 0.000 description 22
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- 238000001953 recrystallisation Methods 0.000 description 11
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- 238000003756 stirring Methods 0.000 description 10
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- 238000001914 filtration Methods 0.000 description 8
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- 239000000725 suspension Substances 0.000 description 8
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- 229960000583 acetic acid Drugs 0.000 description 7
- 239000000908 ammonium hydroxide Substances 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
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- 230000000694 effects Effects 0.000 description 5
- 229910017604 nitric acid Inorganic materials 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
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- 238000011699 spontaneously hypertensive rat Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
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- 125000005843 halogen group Chemical group 0.000 description 4
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- 235000011152 sodium sulphate Nutrition 0.000 description 4
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- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
- NYTBFFZQIRSGLL-UHFFFAOYSA-N 4-isocyanato-1,2-dimethoxybenzene Chemical compound COC1=CC=C(N=C=O)C=C1OC NYTBFFZQIRSGLL-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
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- 230000005484 gravity Effects 0.000 description 3
- AEDIXYWIVPYNBI-UHFFFAOYSA-N heptanamide Chemical compound CCCCCCC(N)=O AEDIXYWIVPYNBI-UHFFFAOYSA-N 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
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- GWTOUXHAXPNJIV-UHFFFAOYSA-N 1-butoxy-2-methoxy-4-nitrobenzene Chemical compound COC1=C(OCCCC)C=CC(=C1)[N+](=O)[O-] GWTOUXHAXPNJIV-UHFFFAOYSA-N 0.000 description 2
- ZDFUQZNBQWTOFG-UHFFFAOYSA-N 2-cyclopentyl-n-[(3,4-dimethoxyphenyl)carbamoyl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1NC(=O)NC(=O)CC1CCCC1 ZDFUQZNBQWTOFG-UHFFFAOYSA-N 0.000 description 2
- NSRHLERHXANNAU-UHFFFAOYSA-N 4-(cyclopentylmethyl)-6,7-dimethoxy-3H-quinazolin-2-one Chemical compound C1(CCCC1)CC1=NC(NC2=CC(=C(C=C12)OC)OC)=O NSRHLERHXANNAU-UHFFFAOYSA-N 0.000 description 2
- UUQWTVAXCHRIKN-UHFFFAOYSA-N 6,7-dihydroxy-4-methyl-3H-quinazolin-2-one hydrate Chemical compound O.OC=1C=C2C(=NC(NC2=CC1O)=O)C UUQWTVAXCHRIKN-UHFFFAOYSA-N 0.000 description 2
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- IVOMOUWHDPKRLL-UHFFFAOYSA-N UNPD107823 Natural products O1C2COP(O)(=O)OC2C(O)C1N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-UHFFFAOYSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 239000000924 antiasthmatic agent Substances 0.000 description 1
- 230000004872 arterial blood pressure Effects 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000004531 blood pressure lowering effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 210000001715 carotid artery Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 1
- 230000004087 circulation Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
- 229940095074 cyclic amp Drugs 0.000 description 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000003979 granulating agent Substances 0.000 description 1
- UCVODTZQZHMTPN-UHFFFAOYSA-N heptanoyl chloride Chemical compound CCCCCCC(Cl)=O UCVODTZQZHMTPN-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/78—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 2
- C07D239/80—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
- C07C205/37—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
- C07C273/1809—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety
- C07C273/1818—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety from -N=C=O and XNR'R"
- C07C273/1827—X being H
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IE34884A IE49470B1 (en) | 1978-12-07 | 1979-12-07 | Substituted quinazolines for the treatment of hypertension and bradycardia and as cardiotonic agents |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US96717378A | 1978-12-07 | 1978-12-07 | |
| US6836779A | 1979-08-21 | 1979-08-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE792364L IE792364L (en) | 1980-06-07 |
| IE49469B1 true IE49469B1 (en) | 1985-10-16 |
Family
ID=26748897
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2364/79A IE49469B1 (en) | 1978-12-07 | 1979-12-07 | Substituted quinazolines |
Country Status (15)
| Country | Link |
|---|---|
| AT (1) | AT374468B (de) |
| AU (1) | AU533427B2 (de) |
| CA (1) | CA1138871A (de) |
| CH (1) | CH645106A5 (de) |
| DE (1) | DE2949395A1 (de) |
| ES (1) | ES486696A0 (de) |
| FR (1) | FR2443462A1 (de) |
| GB (1) | GB2088874B (de) |
| IE (1) | IE49469B1 (de) |
| IL (1) | IL58898A (de) |
| IT (1) | IT1164812B (de) |
| NL (1) | NL7908849A (de) |
| PH (1) | PH16910A (de) |
| PT (1) | PT70559A (de) |
| SE (1) | SE446181B (de) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4631283A (en) * | 1982-09-30 | 1986-12-23 | Ortho Pharmaceutical Corporation | Ortho substituted dihydroxy-2(1H)quinazolinone-1-alkanoic acids |
| US4490374A (en) * | 1982-09-30 | 1984-12-25 | Ortho Pharmaceutical Corporation | 5,6-Dialkoxy-3,4-optionally substituted-2(1H)quinazolinones, composition and method of use |
| US4751304A (en) * | 1984-09-26 | 1988-06-14 | Ortho Pharmaceutical Corporation | Process for preparing 5,6-dialkoxy-4-alkyl-2(1H)-quinazolinones |
| GB0015228D0 (en) * | 2000-06-21 | 2000-08-16 | Portela & Ca Sa | Substituted nitrated catechols, their use in the treatment of some central and peripheral nervous system disorders |
| USD966133S1 (en) * | 2020-09-21 | 2022-10-11 | Aileen Martin | Sanitizer dispenser |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2118315C3 (de) * | 1970-04-20 | 1975-04-03 | Sumitomo Chemical Co., Ltd., Osaka (Japan) | 2-(1H)-Chinazolinonderivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| US4129653A (en) * | 1977-01-05 | 1978-12-12 | Ortho Pharmaceutical Corporation | Substituted pyrrolo [1,2-c] quinazolines and pharmaceutical compositions and methods employing them |
-
1979
- 1979-12-05 AU AU53470/79A patent/AU533427B2/en not_active Ceased
- 1979-12-06 CA CA000341352A patent/CA1138871A/en not_active Expired
- 1979-12-07 IT IT51025/79A patent/IT1164812B/it active
- 1979-12-07 PH PH23380A patent/PH16910A/en unknown
- 1979-12-07 CH CH1090079A patent/CH645106A5/de not_active IP Right Cessation
- 1979-12-07 DE DE19792949395 patent/DE2949395A1/de not_active Ceased
- 1979-12-07 ES ES486696A patent/ES486696A0/es active Granted
- 1979-12-07 SE SE7910105A patent/SE446181B/sv not_active IP Right Cessation
- 1979-12-07 IL IL58898A patent/IL58898A/xx unknown
- 1979-12-07 NL NL7908849A patent/NL7908849A/nl not_active Application Discontinuation
- 1979-12-07 FR FR7930116A patent/FR2443462A1/fr active Granted
- 1979-12-07 IE IE2364/79A patent/IE49469B1/en unknown
- 1979-12-07 PT PT70559A patent/PT70559A/pt unknown
- 1979-12-07 GB GB8138698A patent/GB2088874B/en not_active Expired
- 1979-12-07 AT AT0776379A patent/AT374468B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GB2088874B (en) | 1983-09-28 |
| AT374468B (de) | 1984-04-25 |
| AU533427B2 (en) | 1983-11-24 |
| CA1138871A (en) | 1983-01-04 |
| DE2949395A1 (de) | 1980-06-19 |
| SE7910105L (sv) | 1980-06-08 |
| NL7908849A (nl) | 1980-06-10 |
| FR2443462A1 (fr) | 1980-07-04 |
| IL58898A0 (en) | 1980-03-31 |
| AU5347079A (en) | 1980-06-12 |
| IE792364L (en) | 1980-06-07 |
| IT7951025A0 (it) | 1979-12-07 |
| FR2443462B1 (de) | 1983-09-23 |
| SE446181B (sv) | 1986-08-18 |
| GB2088874A (en) | 1982-06-16 |
| PT70559A (en) | 1980-01-01 |
| ATA776379A (de) | 1983-09-15 |
| IL58898A (en) | 1984-03-30 |
| ES8104253A1 (es) | 1981-04-16 |
| PH16910A (en) | 1984-04-10 |
| ES486696A0 (es) | 1981-04-16 |
| IT1164812B (it) | 1987-04-15 |
| CH645106A5 (de) | 1984-09-14 |
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