NZ196889A - 6-pyrid-(3 or 4)-yl-4,5-dihydropyridazin-3(2h)-ones - Google Patents
6-pyrid-(3 or 4)-yl-4,5-dihydropyridazin-3(2h)-onesInfo
- Publication number
- NZ196889A NZ196889A NZ196889A NZ19688981A NZ196889A NZ 196889 A NZ196889 A NZ 196889A NZ 196889 A NZ196889 A NZ 196889A NZ 19688981 A NZ19688981 A NZ 19688981A NZ 196889 A NZ196889 A NZ 196889A
- Authority
- NZ
- New Zealand
- Prior art keywords
- pyridinyl
- methyl
- acid
- pyridazinone
- dihydro
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 claims description 48
- 150000001875 compounds Chemical class 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- 239000002253 acid Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 239000000243 solution Substances 0.000 claims description 13
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims description 8
- 239000012458 free base Substances 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 6
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 230000000747 cardiac effect Effects 0.000 claims description 5
- 230000003177 cardiotonic effect Effects 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 239000008247 solid mixture Substances 0.000 claims description 3
- WBQLBWAOILVKJU-UHFFFAOYSA-N 2-methyl-4-oxo-4-pyridin-4-ylbutanenitrile Chemical compound N#CC(C)CC(=O)C1=CC=NC=C1 WBQLBWAOILVKJU-UHFFFAOYSA-N 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 3
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- 239000002202 Polyethylene glycol Substances 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
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- 239000000839 emulsion Substances 0.000 claims 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 claims 1
- 229940093471 ethyl oleate Drugs 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 150000002429 hydrazines Chemical class 0.000 claims 1
- 238000010348 incorporation Methods 0.000 claims 1
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- 238000009736 wetting Methods 0.000 claims 1
- 239000000080 wetting agent Substances 0.000 claims 1
- -1 2-substituted-4,5-dihydro-6-(pyridinyl)-3(2H)-pyridazinones Chemical class 0.000 description 33
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- 238000007792 addition Methods 0.000 description 22
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- 238000006243 chemical reaction Methods 0.000 description 20
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- 239000002904 solvent Substances 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
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- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 12
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- WEZLANLGAPCPHL-UHFFFAOYSA-N methyl 4-cyano-2-methyl-4-morpholin-4-yl-4-pyridin-4-ylbutanoate Chemical compound C=1C=NC=CC=1C(C#N)(CC(C)C(=O)OC)N1CCOCC1 WEZLANLGAPCPHL-UHFFFAOYSA-N 0.000 description 9
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 8
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 description 7
- FPZQRPTXDIFAJN-UHFFFAOYSA-N 2,4-dimethyl-6-pyridin-4-yl-4,5-dihydropyridazin-3-one Chemical compound CN1C(=O)C(C)CC(C=2C=CN=CC=2)=N1 FPZQRPTXDIFAJN-UHFFFAOYSA-N 0.000 description 7
- 239000000496 cardiotonic agent Substances 0.000 description 7
- WNDHJGIIUPAEBD-UHFFFAOYSA-N 5-methyl-3-pyridin-4-yl-4,5-dihydro-1h-pyridazin-6-one Chemical compound N1C(=O)C(C)CC(C=2C=CN=CC=2)=N1 WNDHJGIIUPAEBD-UHFFFAOYSA-N 0.000 description 6
- 230000001746 atrial effect Effects 0.000 description 6
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- 238000001704 evaporation Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- IRWZLWUYVNDDIX-UHFFFAOYSA-N 2-methyl-6-pyridin-4-yl-4,5-dihydropyridazin-3-one Chemical compound C1CC(=O)N(C)N=C1C1=CC=NC=C1 IRWZLWUYVNDDIX-UHFFFAOYSA-N 0.000 description 5
- YWJGORHFDXGFTF-UHFFFAOYSA-N 2-methyl-6-pyridin-4-ylpyridazin-3-one Chemical compound C1=CC(=O)N(C)N=C1C1=CC=NC=C1 YWJGORHFDXGFTF-UHFFFAOYSA-N 0.000 description 5
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 5
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
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- 235000014655 lactic acid Nutrition 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- FVBUUYWJAGGTIR-UHFFFAOYSA-N 2-morpholin-4-yl-2-pyridin-4-ylacetonitrile Chemical compound C=1C=NC=CC=1C(C#N)N1CCOCC1 FVBUUYWJAGGTIR-UHFFFAOYSA-N 0.000 description 4
- UTISRGMYIPHHBR-UHFFFAOYSA-N 4-oxo-4-pyridin-4-ylbutanenitrile Chemical compound N#CCCC(=O)C1=CC=NC=C1 UTISRGMYIPHHBR-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
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- 239000007864 aqueous solution Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 229940098779 methanesulfonic acid Drugs 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
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- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
- OASSSUXXWBROIJ-UHFFFAOYSA-N 2-pyridin-4-ylpyridazin-3-one Chemical compound O=C1C=CC=NN1C1=CC=NC=C1 OASSSUXXWBROIJ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
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- 238000010998 test method Methods 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
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- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
- ZFCIFDCCTCGJLX-UHFFFAOYSA-N ethyl 4-cyano-2-methyl-4-morpholin-4-yl-4-pyridin-4-ylbutanoate Chemical compound C=1C=NC=CC=1C(C#N)(CC(C)C(=O)OCC)N1CCOCC1 ZFCIFDCCTCGJLX-UHFFFAOYSA-N 0.000 description 1
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- 125000000623 heterocyclic group Chemical group 0.000 description 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
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- 230000000936 membranestabilizing effect Effects 0.000 description 1
- 229940063557 methacrylate Drugs 0.000 description 1
- SCAVNZFEUOEBQA-UHFFFAOYSA-N methyl 2-methyl-4-oxo-4-pyridin-4-ylbutanoate Chemical compound COC(=O)C(C)CC(=O)C1=CC=NC=C1 SCAVNZFEUOEBQA-UHFFFAOYSA-N 0.000 description 1
- PMOWLRUZAQQLBL-UHFFFAOYSA-N methyl 4-cyano-2-methyl-4-morpholin-4-yl-4-pyridin-3-ylbutanoate Chemical compound C=1C=CN=CC=1C(C#N)(CC(C)C(=O)OC)N1CCOCC1 PMOWLRUZAQQLBL-UHFFFAOYSA-N 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- ZHNFLHYOFXQIOW-LPYZJUEESA-N quinine sulfate dihydrate Chemical compound [H+].[H+].O.O.[O-]S([O-])(=O)=O.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 ZHNFLHYOFXQIOW-LPYZJUEESA-N 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
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 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
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
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- 239000005720 sucrose Substances 0.000 description 1
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- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- ZFDIRQKJPRINOQ-UHFFFAOYSA-N transbutenic acid ethyl ester Natural products CCOC(=O)C=CC ZFDIRQKJPRINOQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/57—Nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14456480A | 1980-04-28 | 1980-04-28 | |
| US06/243,472 US4337253A (en) | 1980-04-28 | 1981-03-13 | 4,5-Dihydro-2-methyl-6-(4-pyridinyl)-3(2H)-pyridazinone and its use as a cardiotonic |
| US06/245,086 US4486431A (en) | 1981-01-14 | 1981-03-18 | Cardiotonic use of 4,5-dihydro-6-(4-pyridinyl)-3(2H)-pyridazinones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ196889A true NZ196889A (en) | 1984-04-27 |
Family
ID=27386124
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ196889A NZ196889A (en) | 1980-04-28 | 1981-04-22 | 6-pyrid-(3 or 4)-yl-4,5-dihydropyridazin-3(2h)-ones |
Country Status (15)
| Country | Link |
|---|---|
| AT (1) | ATA190481A (it) |
| DE (1) | DE3116791A1 (it) |
| DK (1) | DK186781A (it) |
| ES (1) | ES8203880A1 (it) |
| FR (1) | FR2481282A1 (it) |
| GB (1) | GB2076807B (it) |
| IL (1) | IL62679A0 (it) |
| IT (1) | IT1137465B (it) |
| LU (1) | LU83320A1 (it) |
| NL (1) | NL8102078A (it) |
| NO (1) | NO811421L (it) |
| NZ (1) | NZ196889A (it) |
| PH (1) | PH16845A (it) |
| PT (1) | PT72936B (it) |
| SE (1) | SE8102661L (it) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4304777A (en) * | 1979-08-30 | 1981-12-08 | Sterling Drug Inc. | 6-(Pyridinyl)-3(2H)-pyridazinones and their use as cardiotonics |
-
1981
- 1981-04-17 IL IL62679A patent/IL62679A0/xx unknown
- 1981-04-22 NZ NZ196889A patent/NZ196889A/en unknown
- 1981-04-23 GB GB8112639A patent/GB2076807B/en not_active Expired
- 1981-04-24 FR FR8108252A patent/FR2481282A1/fr not_active Withdrawn
- 1981-04-27 PH PH25564A patent/PH16845A/en unknown
- 1981-04-27 PT PT72936A patent/PT72936B/pt unknown
- 1981-04-27 SE SE8102661A patent/SE8102661L/xx not_active Application Discontinuation
- 1981-04-27 DK DK186781A patent/DK186781A/da not_active Application Discontinuation
- 1981-04-27 IT IT21384/81A patent/IT1137465B/it active
- 1981-04-27 NO NO811421A patent/NO811421L/no unknown
- 1981-04-27 ES ES501666A patent/ES8203880A1/es not_active Expired
- 1981-04-28 DE DE19813116791 patent/DE3116791A1/de not_active Withdrawn
- 1981-04-28 AT AT811904A patent/ATA190481A/de not_active IP Right Cessation
- 1981-04-28 NL NL8102078A patent/NL8102078A/nl not_active Application Discontinuation
- 1981-04-28 LU LU83320A patent/LU83320A1/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES501666A0 (es) | 1982-04-01 |
| NL8102078A (nl) | 1981-11-16 |
| DK186781A (da) | 1981-10-29 |
| LU83320A1 (fr) | 1981-12-01 |
| IT1137465B (it) | 1986-09-10 |
| ATA190481A (de) | 1983-12-15 |
| NO811421L (no) | 1981-10-29 |
| GB2076807A (en) | 1981-12-09 |
| DE3116791A1 (de) | 1982-04-15 |
| IT8121384A0 (it) | 1981-04-27 |
| FR2481282A1 (fr) | 1981-10-30 |
| GB2076807B (en) | 1984-03-14 |
| PH16845A (en) | 1984-03-19 |
| ES8203880A1 (es) | 1982-04-01 |
| IL62679A0 (en) | 1981-06-29 |
| PT72936A (en) | 1981-05-01 |
| PT72936B (en) | 1982-04-12 |
| SE8102661L (sv) | 1981-10-29 |
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