NO122375B - - Google Patents

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Info

Publication number: NO122375B
Authority: NO; Norway
Prior art keywords: phenyl; acid; pyridazone; hydrazine; pyridazinone
Prior art date: 1967-05-19

Application number

NO1913/68A

Other languages

English (en)

Norwegian (no)

Inventor

J Baetz

Original Assignee

Seperic

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.)

1967-05-19

Filing date

1968-05-16

Publication date

1971-06-21

1968-05-16 Application filed by Seperic filed Critical Seperic

1971-06-21 Publication of NO122375B publication Critical patent/NO122375B/no

Links

150000001875 compounds Chemical class 0.000 claims description 33
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 21
239000002253 acid Substances 0.000 claims description 19
AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 claims description 11
238000009833 condensation Methods 0.000 claims description 11
230000005494 condensation Effects 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 11
-1 alkyl piperazine Chemical compound 0.000 claims description 10
238000002360 preparation method Methods 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
150000002148 esters Chemical class 0.000 claims description 5
150000004820 halides Chemical class 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 4
238000000034 method Methods 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
150000002431 hydrogen Chemical group 0.000 claims description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
125000003282 alkyl amino group Chemical group 0.000 claims 2
125000003545 alkoxy group Chemical group 0.000 claims 1
125000000217 alkyl group Chemical group 0.000 claims 1
GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 34
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
239000000243 solution Substances 0.000 description 23
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
239000000463 material Substances 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
241000699670 Mus sp. Species 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
239000002585 base Substances 0.000 description 8
238000001035 drying Methods 0.000 description 7
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
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 7
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 6
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 6
QMGVPVSNSZLJIA-FVWCLLPLSA-N strychnine Chemical compound O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
229910052794 bromium Inorganic materials 0.000 description 5
238000002425 crystallisation Methods 0.000 description 5
230000008025 crystallization Effects 0.000 description 5
230000000694 effects Effects 0.000 description 5
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
229910000041 hydrogen chloride Inorganic materials 0.000 description 5
239000000203 mixture Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 4
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
238000001816 cooling Methods 0.000 description 4
238000004821 distillation Methods 0.000 description 4
239000000047 product Substances 0.000 description 4
230000035484 reaction time Effects 0.000 description 4
238000005406 washing Methods 0.000 description 4
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
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 3
241000699666 Mus <mouse, genus> Species 0.000 description 3
QMGVPVSNSZLJIA-UHFFFAOYSA-N Nux Vomica Natural products C1C2C3C4N(C=5C6=CC=CC=5)C(=O)CC3OCC=C2CN2C1C46CC2 QMGVPVSNSZLJIA-UHFFFAOYSA-N 0.000 description 3
LHNKBXRFNPMIBR-UHFFFAOYSA-N Picrotoxin Natural products CC(C)(O)C1(O)C2OC(=O)C1C3(O)C4OC4C5C(=O)OC2C35C LHNKBXRFNPMIBR-UHFFFAOYSA-N 0.000 description 3
241001279009 Strychnos toxifera Species 0.000 description 3
238000001914 filtration Methods 0.000 description 3
150000002429 hydrazines Chemical class 0.000 description 3
239000007924 injection Substances 0.000 description 3
238000002347 injection Methods 0.000 description 3
238000005259 measurement Methods 0.000 description 3
VJKUPQSHOVKBCO-AHMKVGDJSA-N picrotoxin Chemical compound O=C([C@@]12O[C@@H]1C[C@]1(O)[C@@]32C)O[C@@H]3[C@H]2[C@@H](C(=C)C)[C@@H]1C(=O)O2.O=C([C@@]12O[C@@H]1C[C@]1(O)[C@@]32C)O[C@@H]3[C@H]2[C@@H](C(C)(O)C)[C@@H]1C(=O)O2 VJKUPQSHOVKBCO-AHMKVGDJSA-N 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
229960005453 strychnine Drugs 0.000 description 3
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 description 2
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
230000000202 analgesic effect Effects 0.000 description 2
DQFBYFPFKXHELB-UHFFFAOYSA-N chalcone Chemical class C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
239000006260 foam Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
150000003840 hydrochlorides Chemical class 0.000 description 2
229910000042 hydrogen bromide Inorganic materials 0.000 description 2
238000011835 investigation Methods 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000007858 starting material Substances 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
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 1
PRXHANOJNVGVGC-UHFFFAOYSA-N 1,3-bis(4-ethoxyphenyl)thiourea Chemical compound C1=CC(OCC)=CC=C1NC(=S)NC1=CC=C(OCC)C=C1 PRXHANOJNVGVGC-UHFFFAOYSA-N 0.000 description 1
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
BTDANPVPCPUIPF-UHFFFAOYSA-N 3,5-diphenyl-1h-pyridazin-6-one Chemical class O=C1NN=C(C=2C=CC=CC=2)C=C1C1=CC=CC=C1 BTDANPVPCPUIPF-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
206010010904 Convulsion Diseases 0.000 description 1
206010011985 Decubitus ulcer Diseases 0.000 description 1
241000700159 Rattus Species 0.000 description 1
206010039897 Sedation Diseases 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000016571 aggressive behavior Effects 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
230000006399 behavior Effects 0.000 description 1
150000003935 benzaldehydes Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
239000000969 carrier Substances 0.000 description 1
230000002903 catalepsic effect Effects 0.000 description 1
206010007776 catatonia Diseases 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
125000000068 chlorophenyl group Chemical group 0.000 description 1
230000021615 conjugation Effects 0.000 description 1
230000036461 convulsion Effects 0.000 description 1
239000000498 cooling water Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000006356 dehydrogenation reaction Methods 0.000 description 1
238000000280 densification Methods 0.000 description 1
238000010586 diagram Methods 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000003517 fume Substances 0.000 description 1
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
238000007654 immersion Methods 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000007928 intraperitoneal injection Substances 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 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
230000007935 neutral effect Effects 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
230000000506 psychotropic effect Effects 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000007790 scraping Methods 0.000 description 1
238000006748 scratching Methods 0.000 description 1
230000002393 scratching effect Effects 0.000 description 1
230000036280 sedation Effects 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
239000000779 smoke Substances 0.000 description 1
150000003385 sodium Chemical class 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
238000012360 testing method Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

NO1913/68A 1967-05-19 1968-05-16 NO122375B (xx)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB23462/67A GB1157045A (en)	1967-05-19	1967-05-19	Improvements in and relating to New Diphenyl-Pyridazones and process for preparing same

Publications (1)

Publication Number	Publication Date
NO122375B true NO122375B (xx)	1971-06-21

Family

ID=10196018

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO1913/68A NO122375B (xx)	1967-05-19	1968-05-16

Country Status (19)

Country	Link
US (1)	US3622576A (xx)
AT (1)	AT278022B (xx)
BE (1)	BE714796A (xx)
CH (1)	CH493527A (xx)
DE (1)	DE1770429C3 (xx)
DK (1)	DK130587B (xx)
ES (1)	ES354421A1 (xx)
FI (1)	FI48085C (xx)
FR (2)	FR8314M (xx)
GB (1)	GB1157045A (xx)
IE (1)	IE31911B1 (xx)
IL (2)	IL29949A (xx)
IS (1)	IS917B6 (xx)
LU (1)	LU56049A1 (xx)
NL (1)	NL6806824A (xx)
NO (1)	NO122375B (xx)
OA (1)	OA02815A (xx)
SE (1)	SE353324B (xx)
YU (1)	YU33645B (xx)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4258185A (en)	1978-10-17	1981-03-24	Yoshitomi Pharmaceutical Industries, Ltd.	Pyridazinone compounds
EP0442448A3 (en)	1990-02-13	1992-08-12	Bristol-Myers Squibb Company	Heterocyclic carboxylic acids and esters
US4992439A (en) *	1990-02-13	1991-02-12	Bristol-Myers Squibb Company	Pyridazine carboxylic acids and esters
ATE425148T1 (de) *	2000-09-18	2009-03-15	Eisai R&D Man Co Ltd	Triazinone sowie deren medizinale anwendung

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2783232A (en) *		1957-02-26		Pyridazone compounds and their
US3017411A (en) *		1962-01-16		New substituted phthalazones and proc-

1966
- 1966-05-07 IL IL29949A patent/IL29949A/xx unknown
1967
- 1967-05-19 GB GB23462/67A patent/GB1157045A/en not_active Expired
1968
- 1968-05-06 IS IS1740A patent/IS917B6/is unknown
- 1968-05-06 US US726749A patent/US3622576A/en not_active Expired - Lifetime
- 1968-05-07 BE BE714796D patent/BE714796A/xx unknown
- 1968-05-07 IL IL29949A patent/IL29949A0/xx unknown
- 1968-05-08 OA OA53280A patent/OA02815A/xx unknown
- 1968-05-09 LU LU56049D patent/LU56049A1/xx unknown
- 1968-05-13 AT AT458168A patent/AT278022B/de not_active IP Right Cessation
- 1968-05-14 CH CH713968A patent/CH493527A/fr not_active IP Right Cessation
- 1968-05-14 NL NL6806824A patent/NL6806824A/xx unknown
- 1968-05-16 IE IE587/68A patent/IE31911B1/xx unknown
- 1968-05-16 DE DE1770429A patent/DE1770429C3/de not_active Expired
- 1968-05-16 NO NO1913/68A patent/NO122375B/no unknown
- 1968-05-16 FI FI681370A patent/FI48085C/fi active
- 1968-05-17 ES ES354421A patent/ES354421A1/es not_active Expired
- 1968-05-17 FR FR152312A patent/FR8314M/fr not_active Expired
- 1968-05-17 YU YU1161/68A patent/YU33645B/xx unknown
- 1968-05-17 FR FR1567464D patent/FR1567464A/fr not_active Expired
- 1968-05-17 DK DK230868AA patent/DK130587B/da unknown
- 1968-05-20 SE SE06831/68A patent/SE353324B/xx unknown

Also Published As

Publication number	Publication date
FI48085B (xx)	1974-02-28
SE353324B (xx)	1973-01-29
DE1770429B2 (de)	1979-02-22
LU56049A1 (xx)	1968-09-04
DE1770429A1 (de)	1971-10-14
OA02815A (fr)	1970-12-15
FI48085C (fi)	1974-06-10
DK130587B (da)	1975-03-10
ES354421A1 (es)	1969-11-01
DK130587C (xx)	1975-08-18
GB1157045A (en)	1969-07-02
AT278022B (de)	1970-01-26
YU116168A (en)	1977-06-30
FR8314M (xx)	1970-11-30
IS1740A7 (is)	1968-06-14
IE31911B1 (en)	1973-02-07
IS917B6 (is)	1975-12-24
IE31911L (en)	1968-11-19
IL29949A0 (en)	1968-07-25
FR1567464A (xx)	1969-05-16
CH493527A (fr)	1970-07-15
NL6806824A (xx)	1968-11-20
US3622576A (en)	1971-11-23
IL29949A (en)	1971-08-25
DE1770429C3 (de)	1979-10-11
YU33645B (en)	1977-12-31
BE714796A (xx)	1968-09-30

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DK149843B (da)	1986-10-13	Analogifremgangsmaade til fremstilling af 3-substituerede 4-fenylpiperidiner eller salte deraf med farmaceutisk acceptable syrer
Fehnel	1967	Friedländer syntheses with o‐aminoaryl ketones. III. Acid‐catalyzed condensations of o‐aminobenzophenone with polyfunctional carbonyl compounds
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US4188388A (en)	1980-02-12	Phenoxy pyridazinones and anorexigenic use thereof
US2835671A (en)	1958-05-20	Pyridazine derivatives
US3025299A (en)	1962-03-13	New carbostyril derivatives
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CN101870677A (zh)	2010-10-27	一种5-芳甲氧基苯基吡唑类化合物及其制备方法
US4009166A (en)	1977-02-22	Pyrido(2,3-d) pyrimidinones
US4337252A (en)	1982-06-29	1-Phenyl-4-morpholino-1-buten-3-01 derivatives, compositions and use
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De Sarlo et al.	1966	2-Methylisoxazolin-5-ones—II: Ring-opening by bases
Speckamp et al.	1963	Dihydroquinolones I: Reactions of substituted 4‐oxo‐1, 2, 3, 4‐tetrahydroquinoline
NO154840B (no)	1986-09-22	Analogifremgangsmaate til fremstilling av terapeutisk aktive substituerte 2-amino-3,4-dihydropyridinderivater.