DD139578A5 - Verfahren zur herstellung neuer benzopyranderivate - Google Patents
Verfahren zur herstellung neuer benzopyranderivate Download PDFInfo
- Publication number
- DD139578A5 DD139578A5 DD78206709A DD20670978A DD139578A5 DD 139578 A5 DD139578 A5 DD 139578A5 DD 78206709 A DD78206709 A DD 78206709A DD 20670978 A DD20670978 A DD 20670978A DD 139578 A5 DD139578 A5 DD 139578A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- oxo
- benzopyran
- items
- optionally
- carboxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 64
- 150000003839 salts Chemical group 0.000 claims abstract description 67
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 64
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
- 239000001257 hydrogen Substances 0.000 claims abstract description 19
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 17
- 238000002360 preparation method Methods 0.000 claims abstract description 15
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims abstract description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- -1 hydrocarbon radical Chemical class 0.000 claims description 131
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 97
- 150000001875 compounds Chemical class 0.000 claims description 88
- 239000002253 acid Substances 0.000 claims description 39
- 125000004432 carbon atom Chemical group C* 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 125000003545 alkoxy group Chemical group 0.000 claims description 29
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 28
- 229910052736 halogen Inorganic materials 0.000 claims description 24
- 150000002367 halogens Chemical class 0.000 claims description 24
- 125000003431 oxalo group Chemical group 0.000 claims description 19
- 125000002252 acyl group Chemical group 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 15
- 150000003254 radicals Chemical class 0.000 claims description 15
- 125000002947 alkylene group Chemical group 0.000 claims description 14
- 125000001931 aliphatic group Chemical group 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 10
- OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical compound C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 claims description 9
- KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical compound C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 claims description 8
- 150000002431 hydrogen Chemical group 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- CLNIGTPSRSZTRV-UHFFFAOYSA-N 2-oxo-2-[(4-oxochromen-3-yl)amino]acetic acid Chemical class C1=CC=C2C(=O)C(NC(=O)C(=O)O)=COC2=C1 CLNIGTPSRSZTRV-UHFFFAOYSA-N 0.000 claims description 6
- 125000004043 oxo group Chemical group O=* 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
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- UWFGUKKEHDTUHR-UHFFFAOYSA-N 2-[(6-hydroxy-4-oxochromen-3-yl)amino]-2-oxoacetic acid Chemical compound C1=C(O)C=C2C(=O)C(NC(=O)C(=O)O)=COC2=C1 UWFGUKKEHDTUHR-UHFFFAOYSA-N 0.000 claims description 3
- MBTUDAJGCLRFNL-UHFFFAOYSA-N [2-[(2-hydroxyacetyl)amino]-4-oxo-7,8-dihydro-6h-cyclopenta[g]chromen-3-yl] acetate Chemical compound C1=C2C(=O)C(OC(=O)C)=C(NC(=O)CO)OC2=CC2=C1CCC2 MBTUDAJGCLRFNL-UHFFFAOYSA-N 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 150000004820 halides Chemical group 0.000 claims description 3
- IRBBPFRPEUGTRF-UHFFFAOYSA-N n'-(6,7-dimethyl-4-oxochromen-3-yl)oxamide Chemical compound O1C=C(NC(=O)C(N)=O)C(=O)C2=C1C=C(C)C(C)=C2 IRBBPFRPEUGTRF-UHFFFAOYSA-N 0.000 claims description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 150000002905 orthoesters Chemical class 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims 2
- SHQPVTGHIOTYGN-UHFFFAOYSA-N 2-[(6-chloro-8-methyl-4-oxochromen-3-yl)amino]-2-oxoacetic acid Chemical compound ClC=1C=C(C2=C(C(C(=CO2)NC(=O)C(=O)O)=O)C=1)C SHQPVTGHIOTYGN-UHFFFAOYSA-N 0.000 claims 1
- HTXQVFXXVXOLCF-UHFFFAOYSA-N 6-methylchromen-4-one Chemical compound O1C=CC(=O)C2=CC(C)=CC=C21 HTXQVFXXVXOLCF-UHFFFAOYSA-N 0.000 claims 1
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 claims 1
- 238000003797 solvolysis reaction Methods 0.000 claims 1
- 230000003266 anti-allergic effect Effects 0.000 abstract description 4
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 48
- 238000006243 chemical reaction Methods 0.000 description 43
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- 239000000243 solution Substances 0.000 description 30
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
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- 239000004480 active ingredient Substances 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
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- 239000000203 mixture Substances 0.000 description 17
- 239000003795 chemical substances by application Substances 0.000 description 16
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- 125000000350 glycoloyl group Chemical group O=C([*])C([H])([H])O[H] 0.000 description 15
- 238000011282 treatment Methods 0.000 description 15
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
- 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 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 229910052500 inorganic mineral Inorganic materials 0.000 description 12
- 239000011707 mineral Substances 0.000 description 12
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 11
- 239000000460 chlorine Substances 0.000 description 11
- 229910052801 chlorine Inorganic materials 0.000 description 11
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 11
- 239000012442 inert solvent Substances 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
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- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 7
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- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 7
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- 239000003054 catalyst Substances 0.000 description 7
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 7
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- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
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- 208000026935 allergic disease Diseases 0.000 description 5
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- MUCSXJBQZZGOOH-UHFFFAOYSA-N 2-hydroxy-n-(4-oxo-7,8-dihydro-6h-cyclopenta[g]chromen-3-yl)acetamide Chemical compound C1=C2C(=O)C(NC(=O)CO)=COC2=CC2=C1CCC2 MUCSXJBQZZGOOH-UHFFFAOYSA-N 0.000 description 2
- UKXJGSJTACIESA-UHFFFAOYSA-N 2-oxo-2-[(2,6,7-trimethyl-4-oxochromen-3-yl)amino]acetic acid Chemical compound O1C(C)=C(NC(=O)C(O)=O)C(=O)C2=C1C=C(C)C(C)=C2 UKXJGSJTACIESA-UHFFFAOYSA-N 0.000 description 2
- NPMHLDWECTZNTI-UHFFFAOYSA-N 2-oxo-2-[(4-oxo-7,8-dihydro-6h-cyclopenta[g]chromen-3-yl)amino]acetic acid Chemical compound C1=C2C(=O)C(NC(=O)C(=O)O)=COC2=CC2=C1CCC2 NPMHLDWECTZNTI-UHFFFAOYSA-N 0.000 description 2
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- 229940116317 potato starch Drugs 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229940100486 rice starch Drugs 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229940100890 silver compound Drugs 0.000 description 1
- 150000003379 silver compounds Chemical class 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000011697 sodium iodate Substances 0.000 description 1
- 229940032753 sodium iodate Drugs 0.000 description 1
- 235000015281 sodium iodate Nutrition 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical group [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000007056 transamidation reaction Methods 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/94—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrane Compounds (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU77786A LU77786A1 (de) | 1977-07-15 | 1977-07-15 | Verfahren zur herstellung neuer benzopyranderivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD139578A5 true DD139578A5 (de) | 1980-01-09 |
Family
ID=19728641
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD78206709A DD139578A5 (de) | 1977-07-15 | 1978-07-13 | Verfahren zur herstellung neuer benzopyranderivate |
Country Status (19)
| Country | Link |
|---|---|
| US (3) | US4216155A (cs) |
| EP (1) | EP0000488A1 (cs) |
| JP (1) | JPS5419982A (cs) |
| AT (1) | AT363086B (cs) |
| AU (1) | AU3800678A (cs) |
| CS (1) | CS207633B2 (cs) |
| DD (1) | DD139578A5 (cs) |
| DK (1) | DK316178A (cs) |
| ES (1) | ES471696A1 (cs) |
| FI (1) | FI782228A7 (cs) |
| GR (1) | GR72857B (cs) |
| IL (1) | IL55134A0 (cs) |
| LU (1) | LU77786A1 (cs) |
| NO (1) | NO782450L (cs) |
| NZ (1) | NZ187851A (cs) |
| PL (1) | PL208434A1 (cs) |
| PT (1) | PT68289A (cs) |
| SU (1) | SU904521A3 (cs) |
| ZA (1) | ZA784016B (cs) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2861767D1 (en) * | 1977-07-18 | 1982-06-09 | Ciba Geigy Ag | Cephalosprin derivatives, process for their preparation and pharmaceutical compositions containing them |
| EP0078430B2 (de) * | 1981-10-29 | 1993-02-10 | Bayer Ag | Verfahren zur Herstellung von festen, schnellfreisetzenden Arzneizubereitungen mit Dihydropyridinen |
| USRE33963E (en) * | 1981-10-29 | 1992-06-16 | Bayer Aktiengesellschaft | Solid rapidly released medicament preparations containing dihydropyridines, and processes for their preparation |
| JPS5994369A (ja) * | 1982-11-22 | 1984-05-31 | Furukawa Battery Co Ltd:The | アルカリ蓄電池用極板の製造方法 |
| US4614745A (en) * | 1984-04-24 | 1986-09-30 | Ciba-Geigy Corporation | Anti-allergic 3-(carboxycarbonyl)amino benzothiopyran-4-one derivatives, compositions, and method of use therefor |
| US5135754A (en) * | 1988-01-06 | 1992-08-04 | Delalande S.A. | Method of preparing a copolymer of two α-amino acids and a copolymer thus obtained |
| US5579789A (en) * | 1995-01-04 | 1996-12-03 | Whirlpool Corporation | Food soil handling system for a dishwasher |
| KR20170110998A (ko) | 2016-03-24 | 2017-10-12 | 다우 코닝 코포레이션 | 낮은 스토리지 모듈러스 실리콘 기재층을 포함하는 광학용 실리콘 양면 테이프 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3952013A (en) * | 1969-02-12 | 1976-04-20 | Fisons Limited | 1-Thiachromone-2-carboxylic acids and derivatives |
| US3862143A (en) * | 1972-12-04 | 1975-01-21 | Warner Lambert Co | Substituted chromone-3-carbonitriles, carboxamides and carboxylic acids |
| US4007173A (en) * | 1973-05-07 | 1977-02-08 | Smithkline Corporation | α-amino-α-(ureidophenyl)acetamidocephalosporins |
| US3937719A (en) * | 1975-01-06 | 1976-02-10 | American Home Products Corporation | (4-oxo-4h-1-benzopyran-2-yl)-oxamic acid, salts and esters anti-allergic agents |
| US4076729A (en) * | 1976-08-02 | 1978-02-28 | Warner-Lambert Company | (4-Oxo-4H-1-benzopyran-3-yl)aminooxoacetic acids and their derivatives |
| US4313945A (en) * | 1978-11-23 | 1982-02-02 | Ciba-Geigy Corporation | 7-Thiazolyl-acetamido-cephem derivatives with terminal aminocarboxylic acid grouping |
| US4242509A (en) * | 1979-04-13 | 1980-12-30 | Eli Lilly And Company | Process for producing 7-amino-7-alkoxycephalosporins |
-
1977
- 1977-07-15 LU LU77786A patent/LU77786A1/de unknown
-
1978
- 1978-07-07 EP EP78100327A patent/EP0000488A1/de not_active Ceased
- 1978-07-11 US US05/923,522 patent/US4216155A/en not_active Expired - Lifetime
- 1978-07-12 CS CS784665A patent/CS207633B2/cs unknown
- 1978-07-12 FI FI782228A patent/FI782228A7/fi not_active Application Discontinuation
- 1978-07-13 NZ NZ187851A patent/NZ187851A/xx unknown
- 1978-07-13 IL IL55134A patent/IL55134A0/xx unknown
- 1978-07-13 PT PT68289A patent/PT68289A/pt unknown
- 1978-07-13 AU AU38006/78A patent/AU3800678A/en active Pending
- 1978-07-13 DD DD78206709A patent/DD139578A5/de unknown
- 1978-07-13 ES ES471696A patent/ES471696A1/es not_active Expired
- 1978-07-14 NO NO782450A patent/NO782450L/no unknown
- 1978-07-14 ZA ZA00784016A patent/ZA784016B/xx unknown
- 1978-07-14 AT AT0509978A patent/AT363086B/de not_active IP Right Cessation
- 1978-07-14 GR GR56778A patent/GR72857B/el unknown
- 1978-07-14 DK DK783161A patent/DK316178A/da unknown
- 1978-07-15 PL PL20843478A patent/PL208434A1/xx unknown
- 1978-07-15 JP JP8666878A patent/JPS5419982A/ja active Pending
-
1979
- 1979-06-15 SU SU792774403A patent/SU904521A3/ru active
-
1980
- 1980-01-07 US US06/110,077 patent/US4288450A/en not_active Expired - Lifetime
- 1980-02-11 US US06/120,591 patent/US4374134A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| NZ187851A (en) | 1980-05-27 |
| SU904521A3 (ru) | 1982-02-07 |
| CS207633B2 (en) | 1981-08-31 |
| JPS5419982A (en) | 1979-02-15 |
| DK316178A (da) | 1979-01-16 |
| IL55134A0 (en) | 1978-09-29 |
| ES471696A1 (es) | 1979-10-01 |
| US4288450A (en) | 1981-09-08 |
| AT363086B (de) | 1981-07-10 |
| FI782228A7 (fi) | 1979-01-16 |
| LU77786A1 (de) | 1979-03-26 |
| PL208434A1 (pl) | 1979-06-04 |
| GR72857B (cs) | 1983-12-09 |
| PT68289A (de) | 1978-08-01 |
| ZA784016B (en) | 1979-07-25 |
| ATA509978A (de) | 1980-12-15 |
| US4374134A (en) | 1983-02-15 |
| AU3800678A (en) | 1980-01-17 |
| EP0000488A1 (de) | 1979-02-07 |
| NO782450L (no) | 1979-01-16 |
| US4216155A (en) | 1980-08-05 |
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