CS210641B2 - Manufacturing process of 1-methyl-2-/3-sulphamoyl-4-chlor-benzamido/ isoindoline - Google Patents
Manufacturing process of 1-methyl-2-/3-sulphamoyl-4-chlor-benzamido/ isoindoline Download PDFInfo
- Publication number
- CS210641B2 CS210641B2 CS801738A CS173880A CS210641B2 CS 210641 B2 CS210641 B2 CS 210641B2 CS 801738 A CS801738 A CS 801738A CS 173880 A CS173880 A CS 173880A CS 210641 B2 CS210641 B2 CS 210641B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- methyl
- isoindoline
- alpha
- rats
- tert
- Prior art date
Links
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title 1
- QHCAOYAJCBJOLE-UHFFFAOYSA-N 1-methyl-1,3-dihydroisoindol-2-amine;hydrochloride Chemical compound Cl.C1=CC=C2C(C)N(N)CC2=C1 QHCAOYAJCBJOLE-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000004820 halides Chemical class 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 22
- 230000008569 process Effects 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 150000007530 organic bases Chemical class 0.000 claims description 6
- 239000003495 polar organic solvent Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- DKACXUFSLUYRFU-UHFFFAOYSA-N tert-butyl n-aminocarbamate Chemical compound CC(C)(C)OC(=O)NN DKACXUFSLUYRFU-UHFFFAOYSA-N 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 238000004090 dissolution Methods 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- KBVVNGXFPIWMPK-UHFFFAOYSA-N tert-butyl N-(1-methyl-1,3-dihydroisoindol-2-yl)carbamate Chemical compound C1=CC=C2C(C)N(NC(=O)OC(C)(C)C)CC2=C1 KBVVNGXFPIWMPK-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims 1
- 239000002798 polar solvent Substances 0.000 claims 1
- 239000012429 reaction media Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 13
- 230000001882 diuretic effect Effects 0.000 abstract description 13
- 239000002934 diuretic Substances 0.000 abstract description 11
- 230000001077 hypotensive effect Effects 0.000 abstract description 5
- -1 amino compound Chemical class 0.000 abstract description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 2
- MVUYCSCVNPMHPH-UHFFFAOYSA-N 4-chloro-N-(1-methyl-1,3-dihydroisoindol-2-yl)-5-sulfanylidenecyclohexa-1,3-diene-1-carboxamide Chemical compound C1C2=CC=CC=C2C(C)N1NC(=O)C1=CC=C(Cl)C(=S)C1 MVUYCSCVNPMHPH-UHFFFAOYSA-N 0.000 abstract 1
- 239000005711 Benzoic acid Substances 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- 235000010233 benzoic acid Nutrition 0.000 abstract 1
- HBBRVEMMVUOSTL-UHFFFAOYSA-N butyl n-aminocarbamate Chemical compound CCCCOC(=O)NN HBBRVEMMVUOSTL-UHFFFAOYSA-N 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 1
- 241000700159 Rattus Species 0.000 description 40
- NDDAHWYSQHTHNT-UHFFFAOYSA-N indapamide Chemical compound CC1CC2=CC=CC=C2N1NC(=O)C1=CC=C(Cl)C(S(N)(=O)=O)=C1 NDDAHWYSQHTHNT-UHFFFAOYSA-N 0.000 description 22
- 229960004569 indapamide Drugs 0.000 description 22
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 17
- 229910052700 potassium Inorganic materials 0.000 description 17
- 239000011591 potassium Substances 0.000 description 17
- 238000012360 testing method Methods 0.000 description 15
- 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 13
- 229910052708 sodium Inorganic materials 0.000 description 13
- 239000011734 sodium Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 241001465754 Metazoa Species 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 210000002700 urine Anatomy 0.000 description 11
- 230000029142 excretion Effects 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 230000000894 saliuretic effect Effects 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 235000010489 acacia gum Nutrition 0.000 description 6
- 230000037396 body weight Effects 0.000 description 6
- 229920000084 Gum arabic Polymers 0.000 description 5
- 241000978776 Senegalia senegal Species 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 239000000205 acacia gum Substances 0.000 description 5
- 230000003276 anti-hypertensive effect Effects 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- 238000003304 gavage Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000002560 therapeutic procedure Methods 0.000 description 5
- BHUKYXOYJMLRAK-UHFFFAOYSA-N 4-chloro-n-(1-methyl-1,3-dihydroisoindol-2-yl)-3-sulfamoylbenzamide Chemical compound C1C2=CC=CC=C2C(C)N1NC(=O)C1=CC=C(Cl)C(S(N)(=O)=O)=C1 BHUKYXOYJMLRAK-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- 206010020772 Hypertension Diseases 0.000 description 4
- 230000002496 gastric effect Effects 0.000 description 4
- 230000002503 metabolic effect Effects 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 208000004880 Polyuria Diseases 0.000 description 3
- 241000700157 Rattus norvegicus Species 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 210000000936 intestine Anatomy 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 230000002269 spontaneous effect Effects 0.000 description 3
- 210000002784 stomach Anatomy 0.000 description 3
- 230000004873 systolic arterial blood pressure Effects 0.000 description 3
- BPYKTIZUTYGOLE-IFADSCNNSA-N Bilirubin Chemical compound N1C(=O)C(C)=C(C=C)\C1=C\C1=C(C)C(CCC(O)=O)=C(CC2=C(C(C)=C(\C=C/3C(=C(C=C)C(=O)N\3)C)N2)CCC(O)=O)N1 BPYKTIZUTYGOLE-IFADSCNNSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 208000025865 Ulcer Diseases 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 230000004872 arterial blood pressure Effects 0.000 description 2
- 208000037849 arterial hypertension Diseases 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 230000034994 death Effects 0.000 description 2
- 231100000517 death Toxicity 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000035619 diuresis Effects 0.000 description 2
- 229940030606 diuretics Drugs 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 210000004877 mucosa Anatomy 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- CSCPPACGZOOCGX-MICDWDOJSA-N 1-deuteriopropan-2-one Chemical compound [2H]CC(C)=O CSCPPACGZOOCGX-MICDWDOJSA-N 0.000 description 1
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 1
- HXUIDZOMTRMIOE-UHFFFAOYSA-N 3-oxo-3-phenylpropionic acid Chemical compound OC(=O)CC(=O)C1=CC=CC=C1 HXUIDZOMTRMIOE-UHFFFAOYSA-N 0.000 description 1
- 108010082126 Alanine transaminase Proteins 0.000 description 1
- 108010003415 Aspartate Aminotransferases Proteins 0.000 description 1
- 102000004625 Aspartate Aminotransferases Human genes 0.000 description 1
- 208000037157 Azotemia Diseases 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000001785 acacia senegal l. willd gum Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- 208000022531 anorexia Diseases 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- HDWIHXWEUNVBIY-UHFFFAOYSA-N bendroflumethiazidum Chemical compound C1=C(C(F)(F)F)C(S(=O)(=O)N)=CC(S(N2)(=O)=O)=C1NC2CC1=CC=CC=C1 HDWIHXWEUNVBIY-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- JFIOVJDNOJYLKP-UHFFFAOYSA-N bithionol Chemical compound OC1=C(Cl)C=C(Cl)C=C1SC1=CC(Cl)=CC(Cl)=C1O JFIOVJDNOJYLKP-UHFFFAOYSA-N 0.000 description 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 238000009530 blood pressure measurement Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 231100000160 chronic toxicity Toxicity 0.000 description 1
- 230000007665 chronic toxicity Effects 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 206010061428 decreased appetite Diseases 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000000674 effect on sodium Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 235000012631 food intake Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002489 hematologic effect Effects 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 208000036796 hyperbilirubinemia Diseases 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 230000001452 natriuretic effect Effects 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 230000009826 neoplastic cell growth Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 238000001050 pharmacotherapy Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 231100001251 short-term toxicity Toxicity 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 231100000456 subacute toxicity Toxicity 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000003867 tiredness Effects 0.000 description 1
- 208000016255 tiredness Diseases 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000002723 toxicity assay Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- AURFVNDXGLQSNN-UHFFFAOYSA-K trisodium 2-hydroxypropane-1,2,3-tricarboxylic acid phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O.OC(=O)CC(O)(C(O)=O)CC(O)=O AURFVNDXGLQSNN-UHFFFAOYSA-K 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 230000036325 urinary excretion Effects 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
- C07D209/02—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (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)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT20991/79A IT1113879B (it) | 1979-03-15 | 1979-03-15 | Derivato isoindolinico,processo per la sua preparazione e composizioni terapeutiche che lo comprendono come principio attivo |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS210641B2 true CS210641B2 (en) | 1982-01-29 |
Family
ID=11175061
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS801738A CS210641B2 (en) | 1979-03-15 | 1980-03-13 | Manufacturing process of 1-methyl-2-/3-sulphamoyl-4-chlor-benzamido/ isoindoline |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4338331A (it) |
| JP (1) | JPS55127369A (it) |
| AT (1) | AT374179B (it) |
| AU (1) | AU533082B2 (it) |
| BE (1) | BE882239A (it) |
| CA (1) | CA1117130A (it) |
| CS (1) | CS210641B2 (it) |
| DE (1) | DE3009932C2 (it) |
| ES (1) | ES489539A0 (it) |
| FR (1) | FR2451365A1 (it) |
| GB (1) | GB2047241B (it) |
| GR (1) | GR66632B (it) |
| IT (1) | IT1113879B (it) |
| NL (1) | NL8001545A (it) |
| SE (1) | SE8002001L (it) |
| YU (1) | YU70080A (it) |
| ZA (1) | ZA801426B (it) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2654726B1 (fr) * | 1989-11-23 | 1992-02-14 | Rhone Poulenc Sante | Nouveaux derives de l'isoindolone et leur preparation. |
| RU2191572C1 (ru) * | 2001-09-26 | 2002-10-27 | Нестерук Владимир Викторович | Диуретическое и гипотензивное средство в виде таблетки |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL129208C (it) * | 1965-07-14 | |||
| GB1193289A (en) * | 1965-07-14 | 1970-05-28 | Science Union & Cie | New Isoindolino-Sulphonylurea Derivatives and Process for Preparing them |
| FR1557903A (it) * | 1968-01-09 | 1969-02-21 | ||
| GB1203691A (en) * | 1968-03-06 | 1970-09-03 | Science Union & Cie | New disubstituted n-amino indoline derivatives and process for preparing them |
| CH603581A5 (it) * | 1974-03-29 | 1978-08-31 | Siegfried Ag | |
| US4178293A (en) * | 1978-04-14 | 1979-12-11 | Zoecon Corporation | Isoindolinyl derivatives |
-
1979
- 1979-03-15 IT IT20991/79A patent/IT1113879B/it active
-
1980
- 1980-03-11 ZA ZA00801426A patent/ZA801426B/xx unknown
- 1980-03-12 FR FR8005504A patent/FR2451365A1/fr active Granted
- 1980-03-12 GB GB8008368A patent/GB2047241B/en not_active Expired
- 1980-03-13 AU AU56407/80A patent/AU533082B2/en not_active Expired - Fee Related
- 1980-03-13 CS CS801738A patent/CS210641B2/cs unknown
- 1980-03-13 GR GR61432A patent/GR66632B/el unknown
- 1980-03-13 AT AT0139780A patent/AT374179B/de not_active IP Right Cessation
- 1980-03-14 YU YU00700/80A patent/YU70080A/xx unknown
- 1980-03-14 DE DE3009932A patent/DE3009932C2/de not_active Expired
- 1980-03-14 BE BE0/199808A patent/BE882239A/fr not_active IP Right Cessation
- 1980-03-14 ES ES489539A patent/ES489539A0/es active Granted
- 1980-03-14 SE SE8002001A patent/SE8002001L/xx not_active Application Discontinuation
- 1980-03-14 JP JP3171380A patent/JPS55127369A/ja active Pending
- 1980-03-14 CA CA000347681A patent/CA1117130A/en not_active Expired
- 1980-03-14 NL NL8001545A patent/NL8001545A/nl not_active Application Discontinuation
-
1981
- 1981-01-09 US US06/223,798 patent/US4338331A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE3009932C2 (de) | 1983-04-07 |
| YU70080A (en) | 1983-01-21 |
| CA1117130A (en) | 1982-01-26 |
| ATA139780A (de) | 1983-08-15 |
| IT7920991A0 (it) | 1979-03-15 |
| US4338331A (en) | 1982-07-06 |
| NL8001545A (nl) | 1980-09-17 |
| ES8102554A1 (es) | 1981-02-16 |
| SE8002001L (sv) | 1980-09-16 |
| GB2047241B (en) | 1983-01-26 |
| FR2451365B1 (it) | 1983-03-11 |
| FR2451365A1 (fr) | 1980-10-10 |
| GB2047241A (en) | 1980-11-26 |
| JPS55127369A (en) | 1980-10-02 |
| AT374179B (de) | 1984-03-26 |
| IT1113879B (it) | 1986-01-27 |
| GR66632B (it) | 1981-04-03 |
| ZA801426B (en) | 1980-12-31 |
| AU5640780A (en) | 1980-09-18 |
| ES489539A0 (es) | 1981-02-16 |
| DE3009932A1 (de) | 1980-09-25 |
| BE882239A (fr) | 1980-07-01 |
| AU533082B2 (en) | 1983-10-27 |
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