DK141403B - Fremgangsmåde til fremstilling af kinoxalin-1,4-dioxydderivater. - Google Patents
Fremgangsmåde til fremstilling af kinoxalin-1,4-dioxydderivater. Download PDFInfo
- Publication number
- DK141403B DK141403B DK108976AA DK108976A DK141403B DK 141403 B DK141403 B DK 141403B DK 108976A A DK108976A A DK 108976AA DK 108976 A DK108976 A DK 108976A DK 141403 B DK141403 B DK 141403B
- Authority
- DK
- Denmark
- Prior art keywords
- group
- dioxide
- formula
- mole
- carbon atoms
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 18
- CKIHZSGJPSDCNC-UHFFFAOYSA-N Quindoxin Chemical class C1=CC=C2N([O-])C=C[N+](=O)C2=C1 CKIHZSGJPSDCNC-UHFFFAOYSA-N 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 5
- -1 nitrofuryl group Chemical group 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000005936 piperidyl group Chemical group 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 229910052717 sulfur Chemical group 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 31
- JZJFIUXMPBVEFS-UHFFFAOYSA-N 1-oxido-4-oxoquinoxalin-4-ium-2-carbaldehyde Chemical class C1=CC=C2N([O-])C(C=O)=C[N+](=O)C2=C1 JZJFIUXMPBVEFS-UHFFFAOYSA-N 0.000 description 26
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 26
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 150000001299 aldehydes Chemical class 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical class OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 4
- 150000002429 hydrazines Chemical class 0.000 description 4
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 4
- WFJRIDQGVSJLLH-UHFFFAOYSA-N methyl n-aminocarbamate Chemical compound COC(=O)NN WFJRIDQGVSJLLH-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- NZFNXWQNBYZDAQ-UHFFFAOYSA-N thioridazine hydrochloride Chemical compound Cl.C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C NZFNXWQNBYZDAQ-UHFFFAOYSA-N 0.000 description 3
- CWGBFIRHYJNILV-UHFFFAOYSA-N (1,4-diphenyl-1,2,4-triazol-4-ium-3-yl)-phenylazanide Chemical class C=1C=CC=CC=1[N-]C1=NN(C=2C=CC=CC=2)C=[N+]1C1=CC=CC=C1 CWGBFIRHYJNILV-UHFFFAOYSA-N 0.000 description 2
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- PFLUPZGCTVGDLV-UHFFFAOYSA-N acetone azine Chemical compound CC(C)=NN=C(C)C PFLUPZGCTVGDLV-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- QZSYGBNBQHRGKK-ORCRQEGFSA-N (2e)-2-(carbamoylhydrazinylidene)acetic acid Chemical compound NC(=O)N\N=C\C(O)=O QZSYGBNBQHRGKK-ORCRQEGFSA-N 0.000 description 1
- 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
- FZENGILVLUJGJX-IHWYPQMZSA-N (Z)-acetaldehyde oxime Chemical compound C\C=N/O FZENGILVLUJGJX-IHWYPQMZSA-N 0.000 description 1
- HAZRIBSLCUYMQP-UHFFFAOYSA-N 1,2-diaminoguanidine;hydron;chloride Chemical compound Cl.NN\C(N)=N/N HAZRIBSLCUYMQP-UHFFFAOYSA-N 0.000 description 1
- PRPINYUDVPFIRX-UHFFFAOYSA-N 1-naphthaleneacetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CC=CC2=C1 PRPINYUDVPFIRX-UHFFFAOYSA-N 0.000 description 1
- BGRGQBNVLYDHTH-UHFFFAOYSA-N 2,3,4-trimethoxybenzohydrazide Chemical compound COC1=CC=C(C(=O)NN)C(OC)=C1OC BGRGQBNVLYDHTH-UHFFFAOYSA-N 0.000 description 1
- UUPHWTIHFORRJP-UHFFFAOYSA-N 2-aminoguanidine benzaldehyde Chemical compound NNC(=N)N.C(C1=CC=CC=C1)=O UUPHWTIHFORRJP-UHFFFAOYSA-N 0.000 description 1
- FPTCVTJCJMVIDV-UHFFFAOYSA-N 2-phenylacetohydrazide Chemical compound NNC(=O)CC1=CC=CC=C1 FPTCVTJCJMVIDV-UHFFFAOYSA-N 0.000 description 1
- WPBZMCGPFHZRHJ-UHFFFAOYSA-N 4-aminobenzohydrazide Chemical compound NNC(=O)C1=CC=C(N)C=C1 WPBZMCGPFHZRHJ-UHFFFAOYSA-N 0.000 description 1
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
- ZMZGIVVRBMFZSG-UHFFFAOYSA-N 4-hydroxybenzohydrazide Chemical compound NNC(=O)C1=CC=C(O)C=C1 ZMZGIVVRBMFZSG-UHFFFAOYSA-N 0.000 description 1
- YLMBYBOGVUKRGQ-UHFFFAOYSA-N 4-nitro-n-(propan-2-ylideneamino)benzamide Chemical compound CC(C)=NNC(=O)C1=CC=C([N+]([O-])=O)C=C1 YLMBYBOGVUKRGQ-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- VWDLCDMMULGMHS-UHFFFAOYSA-N N-(cyclopentylideneamino)piperidine-4-carboxamide Chemical compound N1CCC(CC1)C(=O)NN=C1CCCC1 VWDLCDMMULGMHS-UHFFFAOYSA-N 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- IUNNCDSJWDQYPW-DJWKRKHSSA-N [(z)-ethylideneamino]urea Chemical compound C\C=N/NC(N)=O IUNNCDSJWDQYPW-DJWKRKHSSA-N 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 150000004705 aldimines Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000003934 aromatic aldehydes Chemical class 0.000 description 1
- 235000013527 bean curd Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- BEYOBVMPDRKTNR-UHFFFAOYSA-N chembl79759 Chemical compound C1=CC(O)=CC=C1N=NC1=CC=CC=C1 BEYOBVMPDRKTNR-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- CGZZMOTZOONQIA-UHFFFAOYSA-N cycloheptanone Chemical compound O=C1CCCCCC1 CGZZMOTZOONQIA-UHFFFAOYSA-N 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- YTQHSQQSLTYMSL-UHFFFAOYSA-N dodecanohydrazide Chemical compound CCCCCCCCCCCC(=O)NN YTQHSQQSLTYMSL-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000000268 heptanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- 150000004658 ketimines Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- BQTYCKJHLIHXHX-UHFFFAOYSA-N n-(benzylideneamino)-3-hydroxynaphthalene-2-carboxamide Chemical compound OC1=CC2=CC=CC=C2C=C1C(=O)NN=CC1=CC=CC=C1 BQTYCKJHLIHXHX-UHFFFAOYSA-N 0.000 description 1
- PROQXPFZMXHCFX-UHFFFAOYSA-N n-(benzylideneamino)-3-nitrobenzamide Chemical compound [O-][N+](=O)C1=CC=CC(C(=O)NN=CC=2C=CC=CC=2)=C1 PROQXPFZMXHCFX-UHFFFAOYSA-N 0.000 description 1
- XZAUWKUFPLFWAI-UHFFFAOYSA-N n-(benzylideneamino)heptanamide Chemical compound CCCCCCC(=O)NN=CC1=CC=CC=C1 XZAUWKUFPLFWAI-UHFFFAOYSA-N 0.000 description 1
- UURXMXQBILMTIB-UHFFFAOYSA-N n-(benzylideneamino)octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NN=CC1=CC=CC=C1 UURXMXQBILMTIB-UHFFFAOYSA-N 0.000 description 1
- BAZGGMGNEFKCHN-UHFFFAOYSA-N n-(benzylideneamino)pyridine-3-carboxamide Chemical compound C=1C=CN=CC=1C(=O)NN=CC1=CC=CC=C1 BAZGGMGNEFKCHN-UHFFFAOYSA-N 0.000 description 1
- UFMAHOLDSCSFMC-UHFFFAOYSA-N n-(benzylideneamino)pyridine-4-carboxamide Chemical compound C=1C=NC=CC=1C(=O)NN=CC1=CC=CC=C1 UFMAHOLDSCSFMC-UHFFFAOYSA-N 0.000 description 1
- DOGVUUYDPVEUHJ-UHFFFAOYSA-N n-(ethylideneamino)-2-hydroxybenzamide Chemical compound CC=NNC(=O)C1=CC=CC=C1O DOGVUUYDPVEUHJ-UHFFFAOYSA-N 0.000 description 1
- RISHSDLMXPLIHT-RVDMUPIBSA-N n-[(e)-benzylideneamino]benzamide Chemical compound C=1C=CC=CC=1C(=O)N\N=C\C1=CC=CC=C1 RISHSDLMXPLIHT-RVDMUPIBSA-N 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical class CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 150000007659 semicarbazones Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/50—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to ring nitrogen atoms
- C07D241/52—Oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/06—Anabolic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Endocrinology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU75EE00002315A HU171738B (hu) | 1975-03-14 | 1975-03-14 | Sposob poluchenija proizvodnykh kinoksalin-1,4-dioksid-azometina |
| HUEE002315 | 1975-03-14 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK108976A DK108976A (enrdf_load_stackoverflow) | 1976-09-15 |
| DK141403B true DK141403B (da) | 1980-03-10 |
| DK141403C DK141403C (enrdf_load_stackoverflow) | 1980-09-08 |
Family
ID=10995603
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK108976AA DK141403B (da) | 1975-03-14 | 1976-03-12 | Fremgangsmåde til fremstilling af kinoxalin-1,4-dioxydderivater. |
Country Status (14)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU184825B (en) * | 1980-09-12 | 1984-10-29 | Egyt Gyogyszervegyeszeti Gyar | Process for preparing new 2-hydroxy-methyl-quinoxaline-1,4-dioxide derivatives |
| HU190795B (en) * | 1982-05-04 | 1986-11-28 | Egyt Gyogyszervegyeszeti Gyar,Hu | Process for producing carbazinic derivatives and compositions containing them for increasing weight yield |
| HU190384B (en) * | 1982-05-04 | 1986-08-28 | Egyt Gyogyszervegyeszeti Gyar,Hu | Process for preparing cycloalkane derivatives and compositions for weight increasing containing such compounds |
| JPH10338673A (ja) * | 1997-06-04 | 1998-12-22 | Nippon Bayeragrochem Kk | イソニコチン酸ヒドラジド誘導体および有害生物防除剤 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3493572A (en) * | 1968-07-05 | 1970-02-03 | Pfizer & Co C | Process for producing quinoxaline-di-n-oxides |
-
1975
- 1975-03-14 HU HU75EE00002315A patent/HU171738B/hu not_active IP Right Cessation
-
1976
- 1976-03-09 CH CH293276A patent/CH601261A5/xx not_active IP Right Cessation
- 1976-03-11 YU YU633/76A patent/YU39478B/xx unknown
- 1976-03-12 SU SU762331905A patent/SU1220570A3/ru active
- 1976-03-12 DD DD191817A patent/DD124382A5/xx not_active IP Right Cessation
- 1976-03-12 CS CS761628A patent/CS208707B2/cs unknown
- 1976-03-12 SE SE7603233A patent/SE424075B/xx not_active IP Right Cessation
- 1976-03-12 FI FI760656A patent/FI61888C/fi not_active IP Right Cessation
- 1976-03-12 DK DK108976AA patent/DK141403B/da not_active IP Right Cessation
- 1976-03-12 GB GB10001/76A patent/GB1537891A/en not_active Expired
- 1976-03-12 AT AT181476A patent/AT352732B/de not_active IP Right Cessation
- 1976-03-13 JP JP51027626A patent/JPS51115485A/ja active Granted
- 1976-03-13 PL PL1976187916A patent/PL98548B1/pl unknown
- 1976-03-15 IN IN455/CAL/76A patent/IN144643B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS51115485A (en) | 1976-10-12 |
| DK141403C (enrdf_load_stackoverflow) | 1980-09-08 |
| SE424075B (sv) | 1982-06-28 |
| CS208707B2 (cs) | 1981-09-15 |
| FI760656A7 (enrdf_load_stackoverflow) | 1976-09-15 |
| PL98548B1 (pl) | 1978-05-31 |
| JPS5725035B2 (enrdf_load_stackoverflow) | 1982-05-27 |
| SU1220570A3 (ru) | 1986-03-23 |
| SE7603233L (sv) | 1976-09-15 |
| DD124382A5 (enrdf_load_stackoverflow) | 1977-02-16 |
| YU39478B (en) | 1984-12-31 |
| ATA181476A (de) | 1979-03-15 |
| GB1537891A (en) | 1979-01-10 |
| FI61888B (fi) | 1982-06-30 |
| IN144643B (enrdf_load_stackoverflow) | 1978-05-27 |
| AT352732B (de) | 1979-10-10 |
| HU171738B (hu) | 1978-03-28 |
| FI61888C (fi) | 1982-10-11 |
| DK108976A (enrdf_load_stackoverflow) | 1976-09-15 |
| CH601261A5 (enrdf_load_stackoverflow) | 1978-06-30 |
| YU63376A (en) | 1982-02-28 |
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