FI70409C - Foerfarande foer framstaellning av ett farmaceutiskt aktivttiofenkarboxamidoetylmerkaptan - Google Patents
Foerfarande foer framstaellning av ett farmaceutiskt aktivttiofenkarboxamidoetylmerkaptan Download PDFInfo
- Publication number
- FI70409C FI70409C FI792476A FI792476A FI70409C FI 70409 C FI70409 C FI 70409C FI 792476 A FI792476 A FI 792476A FI 792476 A FI792476 A FI 792476A FI 70409 C FI70409 C FI 70409C
- Authority
- FI
- Finland
- Prior art keywords
- formula
- compound
- solution
- aktivttiofenkarboxamidoetylmerkaptan
- farmaceutiskt
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 description 16
- 239000000243 solution Substances 0.000 description 15
- 230000000510 mucolytic effect Effects 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 210000002784 stomach Anatomy 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000000843 powder Substances 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- -1 2-thiophenecarboxamidoethyl Chemical group 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 229910001868 water Inorganic materials 0.000 description 4
- 241000251730 Chondrichthyes Species 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 229930006000 Sucrose Natural products 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 210000003097 mucus Anatomy 0.000 description 3
- OYMLNWRWJBYWAB-UHFFFAOYSA-N n-(2-sulfanylethyl)thiophene-2-carboxamide Chemical compound SCCNC(=O)C1=CC=CS1 OYMLNWRWJBYWAB-UHFFFAOYSA-N 0.000 description 3
- 239000005720 sucrose Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- GUCJNQQVGFVQJB-UHFFFAOYSA-N Cl.NCCOC(=S)C1=CC=CS1 Chemical compound Cl.NCCOC(=S)C1=CC=CS1 GUCJNQQVGFVQJB-UHFFFAOYSA-N 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 210000003608 fece Anatomy 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical group CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical compound Cl.NCCS OGMADIBCHLQMIP-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- 229920002556 Polyethylene Glycol 300 Polymers 0.000 description 1
- 206010037368 Pulmonary congestion Diseases 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000003172 expectorant agent Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 230000000762 glandular Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 235000015250 liver sausages Nutrition 0.000 description 1
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L magnesium chloride Substances [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229940066491 mucolytics Drugs 0.000 description 1
- VQLAUZQBHULEDZ-UHFFFAOYSA-N n-(2-sulfanylethyl)benzamide Chemical compound SCCNC(=O)C1=CC=CC=C1 VQLAUZQBHULEDZ-UHFFFAOYSA-N 0.000 description 1
- 239000007923 nasal drop Substances 0.000 description 1
- 229940100662 nasal drops Drugs 0.000 description 1
- 239000007922 nasal spray Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- CRLYFDURCPFDIM-UHFFFAOYSA-N o-(2-aminoethyl) thiophene-2-carbothioate Chemical compound NCCOC(=S)C1=CC=CS1 CRLYFDURCPFDIM-UHFFFAOYSA-N 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 229940068886 polyethylene glycol 300 Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 238000013223 sprague-dawley female rat Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- QIQITDHWZYEEPA-UHFFFAOYSA-N thiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CS1 QIQITDHWZYEEPA-UHFFFAOYSA-N 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US93274678A | 1978-08-10 | 1978-08-10 | |
| US93274678 | 1978-08-10 | ||
| US462279 | 1979-01-18 | ||
| US06/004,622 US4210666A (en) | 1978-08-10 | 1979-01-18 | Mucolytic thiophenecarboxamido alkyl mercaptans |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI792476A FI792476A (fi) | 1980-02-11 |
| FI70409B FI70409B (fi) | 1986-03-27 |
| FI70409C true FI70409C (fi) | 1986-09-19 |
Family
ID=26673251
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI792476A FI70409C (fi) | 1978-08-10 | 1979-08-09 | Foerfarande foer framstaellning av ett farmaceutiskt aktivttiofenkarboxamidoetylmerkaptan |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4210666A (fr) |
| AU (1) | AU521872B2 (fr) |
| CA (1) | CA1124250A (fr) |
| CH (1) | CH641797A5 (fr) |
| DE (1) | DE2932186A1 (fr) |
| DK (1) | DK333579A (fr) |
| EG (1) | EG14406A (fr) |
| ES (2) | ES483271A1 (fr) |
| FI (1) | FI70409C (fr) |
| FR (1) | FR2433019A1 (fr) |
| GB (1) | GB2028326B (fr) |
| IE (1) | IE48795B1 (fr) |
| IL (1) | IL57882A (fr) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL57859A (en) * | 1978-08-10 | 1983-02-23 | Robins Co Inc A H | Salts of benzene and thiophenecarbothioic acid 2-aminoalkyl esters and pharmaceutical compositions containing them |
| IT1226897B (it) * | 1987-09-18 | 1991-02-21 | Richerche Di Schiena Snc Del D | Derivato di taurina, sua preparazione e composizioni farmaceutiche relative |
| US9833207B2 (en) | 2012-08-08 | 2017-12-05 | William Harrison Zurn | Analysis and clearing module, system and method |
| US9962533B2 (en) | 2013-02-14 | 2018-05-08 | William Harrison Zurn | Module for treatment of medical conditions; system for making module and methods of making module |
| EP3797783A1 (fr) | 2019-09-27 | 2021-03-31 | Freie Universität Berlin | Nouvelles utilisations médicales de dérivés de polyglycérol fonctionnalisés de thiol |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3091569A (en) * | 1960-08-26 | 1963-05-28 | Mead Johnson & Co | Mucolytic-nu-acylated sulfhydryl compositions and process for treating animal mucus |
| DE1187605B (de) * | 1963-03-16 | 1965-02-25 | Bayer Ag | Verfahren zur Herstellung von acylierten Alkansulfensaeureamiden |
| US3663690A (en) * | 1969-08-12 | 1972-05-16 | Hoechst Co American | Mucolytic composition and method of treatment of broncho-pulmonary disorders therewith |
| FR2266502A1 (en) * | 1974-04-08 | 1975-10-31 | Synpharm Sa | N-(2-thenoyl)-cysteine and esters - with mucolytic activity, prepd. from cysteine (esters) and thenoyl chloride |
| US4005222A (en) * | 1975-05-21 | 1977-01-25 | Mead Johnson & Company | Mucolytic mercaptoacylamidobenzoic and benzenesulfonic acid compounds and process |
-
1979
- 1979-01-18 US US06/004,622 patent/US4210666A/en not_active Expired - Lifetime
- 1979-07-24 IL IL57882A patent/IL57882A/xx unknown
- 1979-08-03 CH CH717079A patent/CH641797A5/fr not_active IP Right Cessation
- 1979-08-08 DE DE19792932186 patent/DE2932186A1/de active Granted
- 1979-08-08 IE IE1521/79A patent/IE48795B1/en unknown
- 1979-08-08 GB GB7927695A patent/GB2028326B/en not_active Expired
- 1979-08-08 EG EG486/79A patent/EG14406A/xx active
- 1979-08-09 CA CA333,425A patent/CA1124250A/fr not_active Expired
- 1979-08-09 ES ES483271A patent/ES483271A1/es not_active Expired
- 1979-08-09 FI FI792476A patent/FI70409C/fi not_active IP Right Cessation
- 1979-08-09 FR FR7920411A patent/FR2433019A1/fr active Granted
- 1979-08-09 DK DK333579A patent/DK333579A/da not_active Application Discontinuation
- 1979-08-10 AU AU49785/79A patent/AU521872B2/en not_active Ceased
- 1979-11-22 ES ES486227A patent/ES486227A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IL57882A0 (en) | 1979-11-30 |
| DK333579A (da) | 1980-02-11 |
| IE48795B1 (en) | 1985-05-15 |
| GB2028326A (en) | 1980-03-05 |
| DE2932186C2 (fr) | 1988-08-25 |
| AU521872B2 (en) | 1982-05-06 |
| GB2028326B (en) | 1982-12-15 |
| AU4978579A (en) | 1980-02-14 |
| US4210666A (en) | 1980-07-01 |
| IL57882A (en) | 1982-07-30 |
| FI70409B (fi) | 1986-03-27 |
| FI792476A (fi) | 1980-02-11 |
| ES483271A1 (es) | 1980-04-16 |
| CH641797A5 (fr) | 1984-03-15 |
| CA1124250A (fr) | 1982-05-25 |
| DE2932186A1 (de) | 1980-02-14 |
| IE791521L (en) | 1980-02-10 |
| FR2433019A1 (fr) | 1980-03-07 |
| EG14406A (en) | 1984-06-30 |
| FR2433019B1 (fr) | 1982-11-05 |
| ES486227A1 (es) | 1980-06-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: A.H. ROBINS COMPANY, INCORPORATED |