NO119800B - - Google Patents
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- Publication number
- NO119800B NO119800B NO163890A NO16389066A NO119800B NO 119800 B NO119800 B NO 119800B NO 163890 A NO163890 A NO 163890A NO 16389066 A NO16389066 A NO 16389066A NO 119800 B NO119800 B NO 119800B
- Authority
- NO
- Norway
- Prior art keywords
- isoindoline
- methyl
- derivatives
- general formula
- ethanol
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- NKWOXRUJRCMCBH-UHFFFAOYSA-N 1,3-dihydroisoindol-2-amine Chemical compound C1=CC=C2CN(N)CC2=C1 NKWOXRUJRCMCBH-UHFFFAOYSA-N 0.000 claims description 4
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 4
- -1 methyloxy radical Chemical class 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 150000002430 hydrocarbons Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- 239000004202 carbamide Substances 0.000 description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000002218 hypoglycaemic effect Effects 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 235000013877 carbamide Nutrition 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- CTMHWPIWNRWQEG-UHFFFAOYSA-N 1-methylcyclohexene Chemical compound CC1=CCCCC1 CTMHWPIWNRWQEG-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- RUUGNIQERAFPSL-UHFFFAOYSA-N ethyl n-(benzenesulfonyl)carbamate Chemical compound CCOC(=O)NS(=O)(=O)C1=CC=CC=C1 RUUGNIQERAFPSL-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- DDCSCPRXCTVGSD-UHFFFAOYSA-N 2-nitroso-1,3-dihydroisoindole Chemical compound C1=CC=C2CN(N=O)CC2=C1 DDCSCPRXCTVGSD-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
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- JWPWVPPTDSULMI-UHFFFAOYSA-N benzenesulfonamidothiourea Chemical class NC(=S)NNS(=O)(=O)C1=CC=CC=C1 JWPWVPPTDSULMI-UHFFFAOYSA-N 0.000 description 1
- LSNDGFYQJRXEAR-UHFFFAOYSA-N benzenesulfonamidourea Chemical class NC(=O)NNS(=O)(=O)C1=CC=CC=C1 LSNDGFYQJRXEAR-UHFFFAOYSA-N 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- NBEMQPLNBYYUAZ-UHFFFAOYSA-N ethyl acetate;propan-2-one Chemical compound CC(C)=O.CCOC(C)=O NBEMQPLNBYYUAZ-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000009935 nitrosation Effects 0.000 description 1
- 238000007034 nitrosation reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229960005371 tolbutamide Drugs 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C07D209/72—4,7-Endo-alkylene-iso-indoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Analogifremgangsmåte for fremstilling av farmakologisk, særlig hypoglycemisk virksomme N1-isoindolin-N-benzen-sulfonylcarbamid-er.
Nærværende oppfinnelse vedrorer en analogifremgangsmåte for fremstilling av nye derivater av N-arylsulfonyl-N'-(isoindolin-2)-carbamider med den generelle formel:
hvor X betegner
-et hydrogenatom
-et halogenatom
-et metyll-, etyll- eller metylloxyradikal;
og A betegner et cyklisk hydrokarbon fra gruppen omfattende benzen, cyklohexan, endometylen-cyklohexan, endoxo-cyklohexan, cyklohexen, metyll-cyklohexen og endometylen-cyklohexen, så vel som salter av disse derivater med forenbare syrer og baser.
I de franske patenter nr. 1 3<1>+5 329 og 1 357 285 er beskrevet derivater med hypoglycemisk virkning, i det forste patent benzen-sulfonyl semicarbasider og i det annet patent benzen-sulfonyl tiosemicarbasider. I sammenligning med disse kjente forbindelser har forbindelsene som fremstilles ifolge nærværende oppfinnelse en langt sterkere hypoglycemisk virkning.
Ifolge nærværende oppfinnelse fremstilles forbindelsene med formel I ved å omsette et benzen-sulfonyl—uretan med et N-amino-isoindolin etter den metode som er beskrevet av Marshall og medarbeidere i J. Org.Chem. 23_, 927 (1958), idet N-amino-isoindolinet med formelen: hvor A har foran angitte betydning, omsettes med et benzensulf onyl -uretan med formelen:,
hvor X har foran angitte; betydning.
Utgangsforbindolsen N-amirio-isoindolin kan fremstilles ved an-vendelse av metoden av W. Baker og medarbeidere (J. Chem. Soc. 2971 (19^1)), sorn omfatter nitrosering av et isoindolin og reduksjon av N-nitroso-isoindolinet som dannesfmed lithium-alumi nium-hydr i d.
Derivatene som oppnås ifolge oppfinnelsen kan lett erholdes i form av deres addi .<;jonssaltcr enten med egnede syrer eller med baser. Blandt syror som anvendes kan nevnes: saltsyre, brom-hydrogensyre, sulfonsyre, oddiksyre, malonsyre, maleinsyre, fumarsyre, maursyre, eplesyre og andre. Blandt baser kan nevnes hydroxyder av alkali- og jordalkalimetaller, amino-alkoholer' som i'.eks. l-arnino-propanol-2,2-amino-2-metyll-propanol-1 og cholin.
Disse nye derivater og deres addisjonssalter er i besiddelse av viktige terapeutiske egenskaper, særlig hypoglycemiske egenskaper og de kan anvendes som legemidler ved behandling av sukkersyke sammen med egnede farmasøytiske bærestoffer.
Giftigheten for de nye isoindolinsulfonylcarbamider er meget liten. Når mus administreres oralt med 3 g/kg av de nye derivater, iakttaes ingen dodelighet ilopet av KQ timer.
Den hypoglycemiske aktivitet har vært undersokt på rotter og kaniner med doser på 10-25 mg/kg. En betydelig blodsukkersenkning ble oppnådd med alle derivater og utgjorde opp til 53% med 10 mg/kg hos kaniner, og opp til 38% med 25 mg/kg hos rotter.
Til sammenligning forårsaker det velkjente og klinisk meget an-vendte hypoglycemiske "Tolbutamid" med en dose på 25 mg/kg bare en blodsukkersenkning på 19% hos kaniner og 50 nig/kg er nod-vendig for å oppnå en blodsukkersenkning på 23% hos rotter.
De folgende eksempler illustrerer oppfinnelsen. Alle deler er vektsdeler og smeltepunkter er bestemt ved KoTler-metoden.
Eksempel 1
N- (^-- motyll- benzensul (' onyl) - N' - ( isoindolin- 2) - carbamid
Til en suspensjon inneholdende 12,2 deler '(--motyll-benzen-sulfonyluretan og 22 deler toluon tilsettes hurtig 6,7 deler N-amino-isoindolin og 22 deler toluon. I lopet av noen Tå minutter omdannes blandingen til en oppløsning. Opplesningen oppvarmes under tilbakelbp i 2 timer. Don erholdte klare opp-losning krys talliseres ved avkjolning. Krystallene 1'iltreres, vaskes med 8 deler toluon og omkrystalli seres deretter med vannfri othanol.
Det erholdes 9 deler av produktet som smelter ved 198-199°C.
De folgcnde derivater er oppnådd på lignende måte:
a) N-(U—etyll-bonzensulfonyl)-N'-(isoindolin-2)-carbamid - smp.
187°C (methanol) b) N-(<l>+-klor-benzensuli'onyl)-N'-(isoindolin-2)-carbamid - smp.
20r,-207°C (dimetyllformamid-vann) c) N-(benzonsulfonyl)-N'-(isoindolin-2)-carbamid - smp. 200-202°C (ethanol) d) N-Cf-methoxy-benzensulfonyl)-!^1 -(isoindolin-2)-carbamid - smp. 171+-177°C (ethanol) e) N- (^f-metyll-benzensulf onyl) - N' - £( 3c ,'4-,7 ,7c-tetrahydro-isoindolin)- 2j -carbamid - smp. 196-197UC (ethanol) f) N-Ci-klor-bonzonsulf onyl )-I\P - [(3c , 7, 7c-tetrahydro-isoindolin)- 2j-carbamid - smp. 196°C (ethanol) g) N-^-brorri-benzensulfonyl)-!^ ' - [(3c , h, 7 , 7c-tetrahydro-isoindolin)-2j-carbamid - smp. 209-210"C (aceton-etyllacetat) h) N-(>t--e tyll-benden sul fonyl) - N' -[.(3c , 7 , 7c-tetrahydro-isoindolin)-cj-carbamid - smp. lh' y- lh8°C (ethanol)
i ) N- (^-metyll-bcnzensulfonyl ) - N' - [j3c ,'+ ,7 , 7c-tetrahydro-endometylcn-4, 7-isoindolin)-2_j-carbamid - smp. 215-216°C
(dimetyllformamid-vann)
j ) N-(^-metyll-benzensulfonyl )-N'-[(3c,1+,7 ,7c-tetrahydro-endoxo-1+,7-isoindolin)-2j-carbamid - smp. 205-207°C (ethanol) k) N- (^--etyll-benzensulf onyl) -N' - C(3c , 7, 7c-tetrahydro-endoxo-Ll-, 7-isoindolin)-2] -carbamid - smp. 207-208°C (isopropanol)
1) N-(Lt-rnetyll-bonzorisulfonyl)-N' -|j3c 5f 17 57c-tetrahydro-metyll-J-isoindolin)-2j-carbamid - smp. l'/0-171°C (ethanol)
m) N- ('+-me tyll -benzen sul f onyl) - N 1 - (hexahydroisoindolin-2) -
carbamid - smp. 170-172°C (ethanol)
n) N- C-i -klor-benzensulf onyl) - N' - (hexahydroisoindolin-2) - carbamid - smp. 190-191°C (ethanol)
o) N-(V-brom-benzensulfonyl)-N'-(hexahydroisoindolin-2)-carbamid - smp. 211-212°C (ethanol)
p) N- (4--me tyll-benzen sul f onyl) - N' - \_( h, 7-endometylen-hexahydroisoindolin)-2]-carbamid - smp. 199-200°C (ethanol).
Claims (1)
- Analogifremgangsmåte for fremstilling av terapeutisk , særlig hypoglycemisk virksomme isoindolin-2-sulfonylcarbamid-derivater.samt deres salter med syrer og baser-med den generelle formel:hvor X betegner -et hydrogenatom -et halogenatom -et metyll-, etyll- eller metylloxyradikal og A or en hydrokarbonring fra gruppen bony.nriT-cyklohexnn, endometylen-cyklohcxan, endoxo-cyklohexan, cyklohexen, metyll-cyklohexon og endomotylen-cyklohexen,karakterisert vedat ot arylsulfonyluretan med don generelle formel:hvor X har foran angitte betydning, omsettes mod et N-amino-isoindolin med den generelle formel:hvor A har foran angitte betydning og eventuelt omdanner de slik oppnådde derivater til addisjonssalter med forenbare syrer eller baser.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB29841/65A GB1146979A (en) | 1965-07-14 | 1965-07-14 | New isoindolino-sulphonylurea derivatives and process for preparing them |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO119800B true NO119800B (no) | 1970-07-06 |
Family
ID=10298074
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO163890A NO119800B (no) | 1965-07-14 | 1966-07-12 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3503962A (no) |
| AT (1) | AT263800B (no) |
| BE (1) | BE683614A (no) |
| BR (1) | BR6681171D0 (no) |
| CH (1) | CH461500A (no) |
| DE (1) | DE1620393A1 (no) |
| DK (1) | DK118505B (no) |
| ES (1) | ES329130A1 (no) |
| FR (1) | FR5836M (no) |
| GB (1) | GB1146979A (no) |
| NL (2) | NL6608786A (no) |
| NO (1) | NO119800B (no) |
| SE (1) | SE303294B (no) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1113879B (it) * | 1979-03-15 | 1986-01-27 | Farmatis Spa | Derivato isoindolinico,processo per la sua preparazione e composizioni terapeutiche che lo comprendono come principio attivo |
| CN103275058B (zh) * | 2003-08-06 | 2016-02-24 | 西诺米克斯公司 | 调味剂、味道调节剂、促味剂、味觉增强剂、鲜味剂或甜味剂和/或增强剂及其用途 |
| US20060045953A1 (en) * | 2004-08-06 | 2006-03-02 | Catherine Tachdjian | Aromatic amides and ureas and their uses as sweet and/or umami flavor modifiers, tastants and taste enhancers |
| WO2006084184A2 (en) * | 2005-02-04 | 2006-08-10 | Senomyx, Inc. | Molecules comprising linked organic moieties as flavor modifiers for comestible compositions |
| JP4734346B2 (ja) | 2005-02-04 | 2011-07-27 | セノミックス インコーポレイテッド | 連結ヘテロアリール部分を含む化合物、ならびに食用組成物のための新規なうまみフレーバー改変剤、味物質および味覚増強剤としての使用 |
| AR055329A1 (es) * | 2005-06-15 | 2007-08-15 | Senomyx Inc | Amidas bis-aromaticas y sus usos como modificadores de sabor dulce, saborizantes, y realzadores de sabor |
| EP3235811B1 (en) | 2006-04-21 | 2018-07-25 | Senomyx, Inc. | Process of preparing oxalamides |
| MA41553B1 (fr) | 2015-02-16 | 2020-04-30 | The Provost Fellows Found Scholars And The Other Members Of Board Of The College Of The Holy & Undiv | Sulfonylurées, composés apparentés, et leur utilisation |
| DK3661925T3 (da) | 2017-07-07 | 2022-02-28 | Inflazome Ltd | Hidtil ukendte sulfonamidcarboxamidforbindelser |
| US11370776B2 (en) | 2017-07-07 | 2022-06-28 | Inflazome Limited | Sulfonylureas and sulfonylthioureas as NLRP3 inhibitors |
| TW201910314A (zh) * | 2017-08-15 | 2019-03-16 | 愛爾蘭商英弗雷佐姆有限公司 | 新穎化合物 |
| RU2020110219A (ru) | 2017-08-15 | 2021-09-17 | Инфлазоум Лимитед | Сульфонилмочевины и сульфонилтиомочевины в качестве ингибиторов nlrp3 |
| TW201910317A (zh) | 2017-08-15 | 2019-03-16 | 愛爾蘭商英弗雷佐姆有限公司 | 新穎化合物 |
| EP3668843A1 (en) | 2017-08-15 | 2020-06-24 | Inflazome Limited | Sulfonylureas and sulfonylthioureas as nlrp3 inhibitors |
| CN111315733A (zh) | 2017-11-09 | 2020-06-19 | 英夫拉索姆有限公司 | 新颖磺酰胺甲酰胺化合物 |
| US11905252B2 (en) | 2018-03-02 | 2024-02-20 | Inflazome Limited | Compounds |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2408066A (en) * | 1938-05-05 | 1946-09-24 | Hentrich Winfried | P-amino-benzene-sulphamide derivatives |
-
0
- NL NL129208D patent/NL129208C/xx active
-
1965
- 1965-07-14 GB GB29841/65A patent/GB1146979A/en not_active Expired
-
1966
- 1966-06-24 NL NL6608786A patent/NL6608786A/xx unknown
- 1966-06-27 US US560809A patent/US3503962A/en not_active Expired - Lifetime
- 1966-07-04 BE BE683614D patent/BE683614A/xx unknown
- 1966-07-11 BR BR181171/66A patent/BR6681171D0/pt unknown
- 1966-07-12 NO NO163890A patent/NO119800B/no unknown
- 1966-07-12 CH CH1008966A patent/CH461500A/fr unknown
- 1966-07-13 AT AT675266A patent/AT263800B/de active
- 1966-07-14 DK DK365766AA patent/DK118505B/da unknown
- 1966-07-14 SE SE9672/66A patent/SE303294B/xx unknown
- 1966-07-14 ES ES0329130A patent/ES329130A1/es not_active Expired
- 1966-07-14 DE DE19661620393 patent/DE1620393A1/de not_active Withdrawn
- 1966-10-10 FR FR79316A patent/FR5836M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BR6681171D0 (pt) | 1973-12-26 |
| BE683614A (no) | 1967-01-04 |
| DK118505B (da) | 1970-08-31 |
| GB1146979A (en) | 1969-03-26 |
| SE303294B (no) | 1968-08-26 |
| ES329130A1 (es) | 1967-05-01 |
| CH461500A (fr) | 1968-08-31 |
| FR5836M (no) | 1968-03-04 |
| NL129208C (no) | |
| US3503962A (en) | 1970-03-31 |
| DE1620393A1 (de) | 1970-04-02 |
| NL6608786A (no) | 1967-01-16 |
| AT263800B (de) | 1968-08-12 |
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