DK142870B - Analogifremgangsmåde til fremstilling af pyridazinonforbindelser. - Google Patents

Analogifremgangsmåde til fremstilling af pyridazinonforbindelser. Download PDF

Info

Publication number: DK142870B
Authority: DK; Denmark
Prior art keywords: pyridazinone; dihydro; hydroxy; formula; solution
Prior art date: 1973-12-19

Application number

DK634074AA

Other languages

Danish (da)

English (en)

Other versions

DK634074A (fr

DK142870C (fr

Inventor

William John Coates

Robert Antony Slater

Anthony Maitland Roe

Original Assignee

Smith Kline French Lab

Priority date (The priority date 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 date listed.)

1973-12-19

Filing date

1974-12-05

Publication date

1981-02-16

1974-12-05 Application filed by Smith Kline French Lab filed Critical Smith Kline French Lab

1975-08-25 Publication of DK634074A publication Critical patent/DK634074A/da

1981-02-16 Publication of DK142870B publication Critical patent/DK142870B/da

1981-09-21 Application granted granted Critical

1981-09-21 Publication of DK142870C publication Critical patent/DK142870C/da

Links

238000002360 preparation method Methods 0.000 title claims description 29
AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 title claims description 15
238000000034 method Methods 0.000 title claims description 11
230000008569 process Effects 0.000 title claims description 8
-1 nitro, hydroxy Chemical group 0.000 claims description 99
150000001875 compounds Chemical class 0.000 claims description 54
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 34
229910052739 hydrogen Inorganic materials 0.000 claims description 16
239000001257 hydrogen Substances 0.000 claims description 16
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 13
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 12
150000002431 hydrogen Chemical class 0.000 claims description 9
SSDAKJLEKSSAMH-UHFFFAOYSA-N 2,4-dihydro-1h-pyridazin-3-one Chemical compound O=C1CC=CNN1 SSDAKJLEKSSAMH-UHFFFAOYSA-N 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
239000004593 Epoxy Substances 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 5
HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 claims description 5
125000003282 alkyl amino group Chemical group 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
125000003302 alkenyloxy group Chemical group 0.000 claims description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
125000001624 naphthyl group Chemical group 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
125000004417 unsaturated alkyl group Chemical group 0.000 claims description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 120
239000000243 solution Substances 0.000 description 89
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 58
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 56
239000000203 mixture Substances 0.000 description 55
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 51
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
238000010992 reflux Methods 0.000 description 41
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 40
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 38
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 36
239000003921 oil Substances 0.000 description 36
235000019198 oils Nutrition 0.000 description 36
238000001704 evaporation Methods 0.000 description 34
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 33
230000008020 evaporation Effects 0.000 description 33
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 25
238000006243 chemical reaction Methods 0.000 description 22
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 20
238000002844 melting Methods 0.000 description 20
230000008018 melting Effects 0.000 description 20
239000007787 solid Substances 0.000 description 20
235000019260 propionic acid Nutrition 0.000 description 19
239000000377 silicon dioxide Substances 0.000 description 19
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound 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 18
239000000460 chlorine Substances 0.000 description 16
238000001953 recrystallisation Methods 0.000 description 15
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
229960000583 acetic acid Drugs 0.000 description 13
239000000047 product Substances 0.000 description 13
239000012258 stirred mixture Substances 0.000 description 13
238000009835 boiling Methods 0.000 description 11
238000000354 decomposition reaction Methods 0.000 description 11
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 10
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 10
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
239000002585 base Substances 0.000 description 9
239000012362 glacial acetic acid Substances 0.000 description 9
QBQVEOIVSWQRDU-UHFFFAOYSA-N 4-(2-hydroxyphenyl)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)C1=CC=CC=C1O QBQVEOIVSWQRDU-UHFFFAOYSA-N 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
238000002425 crystallisation Methods 0.000 description 8
230000008025 crystallization Effects 0.000 description 8
239000000706 filtrate Substances 0.000 description 8
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 8
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 7
239000000908 ammonium hydroxide Substances 0.000 description 7
230000003276 anti-hypertensive effect Effects 0.000 description 7
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
229910000041 hydrogen chloride Inorganic materials 0.000 description 7
239000000725 suspension Substances 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 6
238000004440 column chromatography Methods 0.000 description 6
238000010828 elution Methods 0.000 description 6
PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 6
239000005457 ice water Substances 0.000 description 6
239000012074 organic phase Substances 0.000 description 6
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 6
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
230000001154 acute effect Effects 0.000 description 5
150000002924 oxiranes Chemical class 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 4
239000002876 beta blocker Substances 0.000 description 4
229940030611 beta-adrenergic blocking agent Drugs 0.000 description 4
230000000903 blocking effect Effects 0.000 description 4
230000000694 effects Effects 0.000 description 4
GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 4
230000032050 esterification Effects 0.000 description 4
238000005886 esterification reaction Methods 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 4
239000000284 extract Substances 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
238000000746 purification Methods 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
235000010288 sodium nitrite Nutrition 0.000 description 4
238000003756 stirring Methods 0.000 description 4
FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 3
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
GMFGICJPHJGECP-UHFFFAOYSA-N 4-(4-fluoro-3-nitrophenyl)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)C1=CC=C(F)C([N+]([O-])=O)=C1 GMFGICJPHJGECP-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
239000011790 ferrous sulphate Substances 0.000 description 3
235000003891 ferrous sulphate Nutrition 0.000 description 3
BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 3
229910000359 iron(II) sulfate Inorganic materials 0.000 description 3
229910017604 nitric acid Inorganic materials 0.000 description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 3
238000000926 separation method Methods 0.000 description 3
239000002904 solvent Substances 0.000 description 3
229940014800 succinic anhydride Drugs 0.000 description 3
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 2
125000006619 (C1-C6) dialkylamino group Chemical group 0.000 description 2
KYEACNNYFNZCST-UHFFFAOYSA-N 1-methylpyrrolidine-2,5-dione Chemical compound CN1C(=O)CCC1=O KYEACNNYFNZCST-UHFFFAOYSA-N 0.000 description 2
KFVDVTYLBHWHHJ-UHFFFAOYSA-N 4-(2-hydroxy-5-nitrophenyl)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)C1=CC([N+]([O-])=O)=CC=C1O KFVDVTYLBHWHHJ-UHFFFAOYSA-N 0.000 description 2
JVHVQJFNBQIPEJ-UHFFFAOYSA-N 4-(2-hydroxyphenyl)-3-methyl-4-oxobutanoic acid Chemical compound OC(=O)CC(C)C(=O)C1=CC=CC=C1O JVHVQJFNBQIPEJ-UHFFFAOYSA-N 0.000 description 2
ZHIWJZMCIFUWSA-UHFFFAOYSA-N 4-(3-amino-4-cyanophenyl)-4-oxobutanoic acid Chemical compound NC1=CC(C(=O)CCC(O)=O)=CC=C1C#N ZHIWJZMCIFUWSA-UHFFFAOYSA-N 0.000 description 2
WRVDYRPIRCXEBN-UHFFFAOYSA-N 4-(3-chloro-2-hydroxyphenyl)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)C1=CC=CC(Cl)=C1O WRVDYRPIRCXEBN-UHFFFAOYSA-N 0.000 description 2
RBRZHQLWTDIFSE-UHFFFAOYSA-N 4-(3-hydroxyphenyl)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)C1=CC=CC(O)=C1 RBRZHQLWTDIFSE-UHFFFAOYSA-N 0.000 description 2
OPMRTOBRNSRRCV-UHFFFAOYSA-N 4-(4-cyano-3-hydroxyphenyl)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)C1=CC=C(C#N)C(O)=C1 OPMRTOBRNSRRCV-UHFFFAOYSA-N 0.000 description 2
FQFAMQRTEAZKKZ-UHFFFAOYSA-N 4-(4-cyano-3-nitrophenyl)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)C1=CC=C(C#N)C([N+]([O-])=O)=C1 FQFAMQRTEAZKKZ-UHFFFAOYSA-N 0.000 description 2
JIGDUCKPRSOOKE-UHFFFAOYSA-N 4-(4-morpholin-4-yl-3-nitrophenyl)-4-oxobutanoic acid Chemical compound [O-][N+](=O)C1=CC(C(=O)CCC(=O)O)=CC=C1N1CCOCC1 JIGDUCKPRSOOKE-UHFFFAOYSA-N 0.000 description 2
RYZPSWSXZLSRHS-UHFFFAOYSA-N 4-(5-amino-2-hydroxyphenyl)-4-oxobutanoic acid Chemical compound NC1=CC=C(O)C(C(=O)CCC(O)=O)=C1 RYZPSWSXZLSRHS-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
241000282326 Felis catus Species 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
206010020772 Hypertension Diseases 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
QGMRQYFBGABWDR-UHFFFAOYSA-M Pentobarbital sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)[N-]C1=O QGMRQYFBGABWDR-UHFFFAOYSA-M 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
208000001871 Tachycardia Diseases 0.000 description 2
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
238000001816 cooling Methods 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical group [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
229960001317 isoprenaline Drugs 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
ZOOTXGXHWQPRGE-UHFFFAOYSA-N methyl 4-(2-hydroxyphenyl)-4-oxobutanoate Chemical compound COC(=O)CCC(=O)C1=CC=CC=C1O ZOOTXGXHWQPRGE-UHFFFAOYSA-N 0.000 description 2
HGNUIJAOYARUND-UHFFFAOYSA-N methyl 4-(3-hydroxyphenyl)-4-oxobutanoate Chemical compound COC(=O)CCC(=O)C1=CC=CC(O)=C1 HGNUIJAOYARUND-UHFFFAOYSA-N 0.000 description 2
LVHWYFLZVALMGD-UHFFFAOYSA-N methyl 4-(5-acetamido-2-hydroxyphenyl)-4-oxobutanoate Chemical compound COC(=O)CCC(=O)C1=CC(NC(C)=O)=CC=C1O LVHWYFLZVALMGD-UHFFFAOYSA-N 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000002243 precursor Substances 0.000 description 2
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 2
229940080818 propionamide Drugs 0.000 description 2
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
239000002002 slurry Substances 0.000 description 2
230000006794 tachycardia Effects 0.000 description 2
125000004890 (C1-C6) alkylamino group Chemical group 0.000 description 1
OUQSGILAXUXMGI-UHFFFAOYSA-N 1-bromo-4-phenylmethoxybenzene Chemical compound C1=CC(Br)=CC=C1OCC1=CC=CC=C1 OUQSGILAXUXMGI-UHFFFAOYSA-N 0.000 description 1
MBCBBSHNMFQVLM-UHFFFAOYSA-N 2-[3-(tert-butylamino)-2-hydroxypropoxy]-4-(6-oxo-4,5-dihydro-1H-pyridazin-3-yl)benzonitrile Chemical compound C1=C(C#N)C(OCC(O)CNC(C)(C)C)=CC(C=2CCC(=O)NN=2)=C1 MBCBBSHNMFQVLM-UHFFFAOYSA-N 0.000 description 1
NHLRXJOXXOVFJM-UHFFFAOYSA-N 2-[3-(tert-butylamino)-2-hydroxypropoxy]-5-(6-oxo-4,5-dihydro-1H-pyridazin-3-yl)benzonitrile Chemical compound C1=C(C#N)C(OCC(O)CNC(C)(C)C)=CC=C1C1=NNC(=O)CC1 NHLRXJOXXOVFJM-UHFFFAOYSA-N 0.000 description 1
ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
WLVPRARCUSRDNI-UHFFFAOYSA-N 2-hydroxy-1-phenyl-1-propanone Chemical compound CC(O)C(=O)C1=CC=CC=C1 WLVPRARCUSRDNI-UHFFFAOYSA-N 0.000 description 1
CHZCERSEMVWNHL-UHFFFAOYSA-N 2-hydroxybenzonitrile Chemical compound OC1=CC=CC=C1C#N CHZCERSEMVWNHL-UHFFFAOYSA-N 0.000 description 1
CNQOORHYEKAWRC-UHFFFAOYSA-N 3,3,3-trifluoro-2-oxopropanal Chemical compound FC(F)(F)C(=O)C=O CNQOORHYEKAWRC-UHFFFAOYSA-N 0.000 description 1
BJPZAPQSNTVTAU-UHFFFAOYSA-N 3-(3-fluoro-4-hydroxyphenyl)-4,5-dihydro-1H-pyridazin-6-one Chemical compound C1=C(F)C(O)=CC=C1C1=NNC(=O)CC1 BJPZAPQSNTVTAU-UHFFFAOYSA-N 0.000 description 1
XNEWOEPMKIKENL-UHFFFAOYSA-N 3-(3-hydroxy-4-morpholin-4-ylphenyl)-4,5-dihydro-1h-pyridazin-6-one Chemical compound OC1=CC(C=2CCC(=O)NN=2)=CC=C1N1CCOCC1 XNEWOEPMKIKENL-UHFFFAOYSA-N 0.000 description 1
QKNCASVNQDXUFI-UHFFFAOYSA-N 3-(3-hydroxyphenyl)-4,5-dihydro-1h-pyridazin-6-one Chemical compound OC1=CC=CC(C=2CCC(=O)NN=2)=C1 QKNCASVNQDXUFI-UHFFFAOYSA-N 0.000 description 1
RVPMVLGLKPQBHA-UHFFFAOYSA-N 3-(dimethylamino)-1-(2-hydroxyphenyl)-2-methylpropan-1-one Chemical compound CN(C)CC(C)C(=O)C1=CC=CC=C1O RVPMVLGLKPQBHA-UHFFFAOYSA-N 0.000 description 1
MBJFDZLOIJIUPC-UHFFFAOYSA-N 3-[4-(oxiran-2-ylmethoxy)phenyl]-4,5-dihydro-1h-pyridazin-6-one Chemical compound N1C(=O)CCC(C=2C=CC(OCC3OC3)=CC=2)=N1 MBJFDZLOIJIUPC-UHFFFAOYSA-N 0.000 description 1
OOGOFUKAJDPHDJ-UHFFFAOYSA-N 3-fluoro-4-hydroxy-5-methoxybenzaldehyde Chemical group COC1=CC(C=O)=CC(F)=C1O OOGOFUKAJDPHDJ-UHFFFAOYSA-N 0.000 description 1
125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 1
PLUHHWJZORAODT-UHFFFAOYSA-N 3-methyl-4-oxo-4-(2-phenylmethoxyphenyl)butanenitrile Chemical compound N#CCC(C)C(=O)C1=CC=CC=C1OCC1=CC=CC=C1 PLUHHWJZORAODT-UHFFFAOYSA-N 0.000 description 1
VEMILKYHFUPAJA-UHFFFAOYSA-N 4-(2-hydroxy-4-methylphenyl)-4-oxobutanoic acid Chemical compound CC1=CC=C(C(=O)CCC(O)=O)C(O)=C1 VEMILKYHFUPAJA-UHFFFAOYSA-N 0.000 description 1
LKCLKCOWTYSINF-UHFFFAOYSA-N 4-(2-hydroxy-5-methoxyphenyl)-4-oxobutanoic acid Chemical compound COC1=CC=C(O)C(C(=O)CCC(O)=O)=C1 LKCLKCOWTYSINF-UHFFFAOYSA-N 0.000 description 1
NUMGKJNSGGELIA-UHFFFAOYSA-N 4-(2-hydroxy-5-methylphenyl)-4-oxobutanoic acid Chemical compound CC1=CC=C(O)C(C(=O)CCC(O)=O)=C1 NUMGKJNSGGELIA-UHFFFAOYSA-N 0.000 description 1
NTTLPOXDWCRJMH-UHFFFAOYSA-N 4-(3-amino-4-ethylphenyl)-4-oxobutanoic acid Chemical compound NC=1C=C(C(=O)CCC(=O)O)C=CC1CC NTTLPOXDWCRJMH-UHFFFAOYSA-N 0.000 description 1
MUQBDZJZOVKQFB-UHFFFAOYSA-N 4-(3-amino-4-morpholin-4-ylphenyl)-4-oxobutanoic acid Chemical compound NC1=CC(C(=O)CCC(O)=O)=CC=C1N1CCOCC1 MUQBDZJZOVKQFB-UHFFFAOYSA-N 0.000 description 1
SNRFVYKMDZSFED-UHFFFAOYSA-N 4-(3-fluoro-4-methoxyphenyl)-4-oxobutanoic acid Chemical compound COC1=CC=C(C(=O)CCC(O)=O)C=C1F SNRFVYKMDZSFED-UHFFFAOYSA-N 0.000 description 1
QQKPYQZJNRMDKN-UHFFFAOYSA-N 4-(3-hydroxy-2-nitrophenyl)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)C1=CC=CC(O)=C1[N+]([O-])=O QQKPYQZJNRMDKN-UHFFFAOYSA-N 0.000 description 1
SSWTVKKFWKJDHO-UHFFFAOYSA-N 4-(4-amino-3-nitrophenyl)-4-oxobutanoic acid Chemical compound NC1=CC=C(C(=O)CCC(O)=O)C=C1[N+]([O-])=O SSWTVKKFWKJDHO-UHFFFAOYSA-N 0.000 description 1
IONZSSONOSWCHT-UHFFFAOYSA-N 4-(4-ethyl-3-nitrophenyl)-4-oxobutanoic acid Chemical compound C(C)C1=C(C=C(C(=O)CCC(=O)O)C=C1)[N+](=O)[O-] IONZSSONOSWCHT-UHFFFAOYSA-N 0.000 description 1
WUYWHIAAQYQKPP-UHFFFAOYSA-N 4-(4-fluorophenyl)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)C1=CC=C(F)C=C1 WUYWHIAAQYQKPP-UHFFFAOYSA-N 0.000 description 1
RVDWUHPNGCQYRK-UHFFFAOYSA-N 4-(4-hydroxy-3-methylphenyl)-4-oxobutanoic acid Chemical compound CC1=CC(C(=O)CCC(O)=O)=CC=C1O RVDWUHPNGCQYRK-UHFFFAOYSA-N 0.000 description 1
YBSVOTYKOZVOIJ-UHFFFAOYSA-N 4-(5-chloro-2-hydroxyphenyl)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)C1=CC(Cl)=CC=C1O YBSVOTYKOZVOIJ-UHFFFAOYSA-N 0.000 description 1
GEGQHBJMVLXZQV-UHFFFAOYSA-N 4-(5-fluoro-2-hydroxyphenyl)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)C1=CC(F)=CC=C1O GEGQHBJMVLXZQV-UHFFFAOYSA-N 0.000 description 1
OWYONAOVTVFEBP-UHFFFAOYSA-N 5-hydroxy-1-methyl-5-(4-phenylmethoxyphenyl)pyrrolidin-2-one Chemical compound CN1C(=O)CCC1(O)C(C=C1)=CC=C1OCC1=CC=CC=C1 OWYONAOVTVFEBP-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
206010002383 Angina Pectoris Diseases 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
239000007818 Grignard reagent Substances 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
235000019502 Orange oil Nutrition 0.000 description 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
229930040373 Paraformaldehyde Natural products 0.000 description 1
241000700159 Rattus Species 0.000 description 1
206010047141 Vasodilatation Diseases 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000002220 antihypertensive agent Substances 0.000 description 1
229940030600 antihypertensive agent Drugs 0.000 description 1
206010003119 arrhythmia Diseases 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
239000004327 boric acid Substances 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
125000005587 carbonate group Chemical group 0.000 description 1
JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
ZGNIYAPHJAPRMA-UHFFFAOYSA-N chlorine azide Chemical compound ClN=[N+]=[N-] ZGNIYAPHJAPRMA-UHFFFAOYSA-N 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
239000012043 crude product Substances 0.000 description 1
LYZCWDIVOAXKQP-UHFFFAOYSA-N diazinan-3-one Chemical compound O=C1CCCNN1 LYZCWDIVOAXKQP-UHFFFAOYSA-N 0.000 description 1
239000012954 diazonium Substances 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical group [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
231100000673 dose–response relationship Toxicity 0.000 description 1
RUYBXJYVHYDTQL-UHFFFAOYSA-N ethyl 4-(3,4-dimethoxyphenyl)-4-oxobutanoate Chemical compound CCOC(=O)CCC(=O)C1=CC=C(OC)C(OC)=C1 RUYBXJYVHYDTQL-UHFFFAOYSA-N 0.000 description 1
VOBJDVORMSMFSD-UHFFFAOYSA-N ethyl 4-(4-chloro-2-hydroxyphenyl)-4-oxobutanoate Chemical compound CCOC(=O)CCC(=O)C1=CC=C(Cl)C=C1O VOBJDVORMSMFSD-UHFFFAOYSA-N 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
239000006260 foam Substances 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
150000004795 grignard reagents Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000004688 heptahydrates Chemical class 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000003840 hydrochlorides Chemical group 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
150000001261 hydroxy acids Chemical class 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
230000001631 hypertensive effect Effects 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
210000003141 lower extremity Anatomy 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
MEQVMVVOUNBUPM-UHFFFAOYSA-N methyl 4-(3-chloro-2-hydroxyphenyl)-4-oxobutanoate Chemical compound COC(=O)CCC(=O)C1=CC=CC(Cl)=C1O MEQVMVVOUNBUPM-UHFFFAOYSA-N 0.000 description 1
VRURQOFXQLLBNT-UHFFFAOYSA-N n-[4-[3-(tert-butylamino)-2-hydroxypropoxy]-3-(6-oxo-4,5-dihydro-1h-pyridazin-3-yl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=C(OCC(O)CNC(C)(C)C)C(C=2CCC(=O)NN=2)=C1 VRURQOFXQLLBNT-UHFFFAOYSA-N 0.000 description 1
229940105631 nembutal Drugs 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
229920002866 paraformaldehyde Polymers 0.000 description 1
230000037361 pathway Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
239000000843 powder Substances 0.000 description 1
150000004672 propanoic acids Chemical class 0.000 description 1
DSNYFFJTZPIKFZ-UHFFFAOYSA-N propoxybenzene Chemical group CCCOC1=CC=CC=C1 DSNYFFJTZPIKFZ-UHFFFAOYSA-N 0.000 description 1
230000009467 reduction Effects 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
238000001256 steam distillation Methods 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 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 description 1
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
230000024883 vasodilation Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
- 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
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- 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
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/38—2-Pyrrolones
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DK634074AA 1973-12-19 1974-12-05 Analogifremgangsmåde til fremstilling af pyridazinonforbindelser. DK142870B (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB58726/73A GB1488330A (en)	1973-12-19	1973-12-19	Dihydropyridazinones
GB5872673		1973-12-19

Publications (3)

Publication Number	Publication Date
DK634074A DK634074A (fr)	1975-08-25
DK142870B true DK142870B (da)	1981-02-16
DK142870C DK142870C (fr)	1981-09-21

Family

ID=10482281

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK634074AA DK142870B (da)	1973-12-19	1974-12-05	Analogifremgangsmåde til fremstilling af pyridazinonforbindelser.

Country Status (18)

Country	Link
US (1)	US3931177A (fr)
JP (1)	JPS5093984A (fr)
BE (1)	BE823103A (fr)
CA (1)	CA1033733A (fr)
CH (1)	CH608794A5 (fr)
DE (1)	DE2459468A1 (fr)
DK (1)	DK142870B (fr)
ES (1)	ES433135A1 (fr)
FI (1)	FI356974A7 (fr)
FR (1)	FR2255070B1 (fr)
GB (1)	GB1488330A (fr)
HU (1)	HU170633B (fr)
IE (1)	IE40428B1 (fr)
IL (1)	IL46158A (fr)
NL (1)	NL7416578A (fr)
SE (1)	SE413405B (fr)
SU (1)	SU578872A3 (fr)
ZA (1)	ZA747462B (fr)

Families Citing this family (25)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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1973
- 1973-12-19 GB GB58726/73A patent/GB1488330A/en not_active Expired
1974
- 1974-11-21 ZA ZA00747462A patent/ZA747462B/xx unknown
- 1974-11-27 CA CA214,774A patent/CA1033733A/fr not_active Expired
- 1974-11-29 IE IE2477/74A patent/IE40428B1/xx unknown
- 1974-11-29 IL IL46158A patent/IL46158A/xx unknown
- 1974-12-05 DK DK634074AA patent/DK142870B/da unknown
- 1974-12-09 BE BE151287A patent/BE823103A/fr not_active IP Right Cessation
- 1974-12-11 FI FI3569/74A patent/FI356974A7/fi unknown
- 1974-12-12 US US05/531,957 patent/US3931177A/en not_active Expired - Lifetime
- 1974-12-13 SE SE7415691A patent/SE413405B/xx unknown
- 1974-12-16 DE DE19742459468 patent/DE2459468A1/de not_active Ceased
- 1974-12-17 FR FR7441471A patent/FR2255070B1/fr not_active Expired
- 1974-12-17 CH CH7416775A patent/CH608794A5/xx not_active IP Right Cessation
- 1974-12-18 SU SU7402088301A patent/SU578872A3/ru active
- 1974-12-18 JP JP49146279A patent/JPS5093984A/ja active Pending
- 1974-12-18 HU HUSI1445A patent/HU170633B/hu unknown
- 1974-12-19 NL NL7416578A patent/NL7416578A/xx not_active Application Discontinuation
- 1974-12-19 ES ES433135A patent/ES433135A1/es not_active Expired

Also Published As

Publication number	Publication date
CH608794A5 (fr)	1979-01-31
DK634074A (fr)	1975-08-25
IE40428L (en)	1975-06-19
IE40428B1 (en)	1979-05-23
SE413405B (sv)	1980-05-27
FI356974A7 (fr)	1975-06-20
SU578872A3 (ru)	1977-10-30
NL7416578A (nl)	1975-06-23
CA1033733A (fr)	1978-06-27
DK142870C (fr)	1981-09-21
DE2459468A1 (de)	1975-07-03
SE7415691L (fr)	1975-06-23
ES433135A1 (es)	1976-11-16
US3931177A (en)	1976-01-06
HU170633B (fr)	1977-07-28
AU7572474A (en)	1976-05-27
BE823103A (fr)	1975-06-09
FR2255070B1 (fr)	1979-09-21
FR2255070A1 (fr)	1975-07-18
ZA747462B (en)	1975-12-31
GB1488330A (en)	1977-10-12
IL46158A0 (en)	1975-02-10
JPS5093984A (fr)	1975-07-26
IL46158A (en)	1978-08-31

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