FI69060C - Foerfarande foer framstaellning av ett farmaceutiskt aktivt 2-minoetylestersyrasalt av en substituerad bensen- eller os ubtituerad tiofenkarbotioinsyra - Google Patents
Foerfarande foer framstaellning av ett farmaceutiskt aktivt 2-minoetylestersyrasalt av en substituerad bensen- eller os ubtituerad tiofenkarbotioinsyra Download PDFInfo
- Publication number
- FI69060C FI69060C FI792474A FI792474A FI69060C FI 69060 C FI69060 C FI 69060C FI 792474 A FI792474 A FI 792474A FI 792474 A FI792474 A FI 792474A FI 69060 C FI69060 C FI 69060C
- Authority
- FI
- Finland
- Prior art keywords
- ubtituerad
- tiofenkarbotioinsyra
- estersyrasal
- framstation
- minoethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 description 12
- 210000002784 stomach Anatomy 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical compound Cl.NCCS OGMADIBCHLQMIP-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 229930006000 Sucrose Natural products 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 230000000510 mucolytic effect Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000005720 sucrose Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 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 3
- -1 bromo, chloro, iodo, methoxy, ethoxy Chemical group 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 210000003097 mucus Anatomy 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 2
- JGYPCVMXENEIIE-UHFFFAOYSA-N Cl.NCCOC(=S)C1=CC=C(Cl)C=C1 Chemical compound Cl.NCCOC(=S)C1=CC=C(Cl)C=C1 JGYPCVMXENEIIE-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000003172 expectorant agent Substances 0.000 description 2
- 210000003608 fece Anatomy 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 229940066491 mucolytics Drugs 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- ZQXIMYREBUZLPM-UHFFFAOYSA-N 1-aminoethanethiol Chemical compound CC(N)S ZQXIMYREBUZLPM-UHFFFAOYSA-N 0.000 description 1
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
- YGAPOICUMNPIPF-UHFFFAOYSA-N 4-methoxybenzenecarbothioic s-acid Chemical compound COC1=CC=C(C(S)=O)C=C1 YGAPOICUMNPIPF-UHFFFAOYSA-N 0.000 description 1
- PJHWTWHVCOZCPU-UHFFFAOYSA-N 4-methylbenzenecarbothioic s-acid Chemical compound CC1=CC=C(C(O)=S)C=C1 PJHWTWHVCOZCPU-UHFFFAOYSA-N 0.000 description 1
- NQUVCRCCRXRJCK-UHFFFAOYSA-N 4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1 NQUVCRCCRXRJCK-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- GUCJNQQVGFVQJB-UHFFFAOYSA-N Cl.NCCOC(=S)C1=CC=CS1 Chemical compound Cl.NCCOC(=S)C1=CC=CS1 GUCJNQQVGFVQJB-UHFFFAOYSA-N 0.000 description 1
- 208000019693 Lung disease Diseases 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
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- 230000003187 abdominal effect Effects 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 229960004308 acetylcysteine Drugs 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- MXMOTZIXVICDSD-UHFFFAOYSA-N anisoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1 MXMOTZIXVICDSD-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 230000000762 glandular Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L magnesium chloride Substances [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- ZSCGMTWBDWARBZ-UHFFFAOYSA-N o-(2-aminoethyl) benzenecarbothioate;hydrochloride Chemical compound Cl.NCCOC(=S)C1=CC=CC=C1 ZSCGMTWBDWARBZ-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 238000013223 sprague-dawley female rat Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000003786 synthesis reaction 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
- 238000001665 trituration Methods 0.000 description 1
- 238000005406 washing 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/10—Expectorants
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US93274778A | 1978-08-10 | 1978-08-10 | |
| US93274778 | 1978-08-10 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI792474A7 FI792474A7 (fi) | 1980-02-11 |
| FI69060B FI69060B (fi) | 1985-08-30 |
| FI69060C true FI69060C (fi) | 1985-12-10 |
Family
ID=25462846
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI792474A FI69060C (fi) | 1978-08-10 | 1979-08-09 | Foerfarande foer framstaellning av ett farmaceutiskt aktivt 2-minoetylestersyrasalt av en substituerad bensen- eller os ubtituerad tiofenkarbotioinsyra |
Country Status (17)
| Country | Link |
|---|---|
| JP (2) | JPS5536486A (en, 2012) |
| AU (1) | AU520791B2 (en, 2012) |
| BE (1) | BE878169A (en, 2012) |
| CA (1) | CA1125297A (en, 2012) |
| CH (1) | CH642062A5 (en, 2012) |
| DE (1) | DE2932402A1 (en, 2012) |
| DK (1) | DK159655C (en, 2012) |
| EG (1) | EG14416A (en, 2012) |
| ES (1) | ES483269A1 (en, 2012) |
| FI (1) | FI69060C (en, 2012) |
| FR (2) | FR2433016A1 (en, 2012) |
| GB (1) | GB2028325B (en, 2012) |
| IE (1) | IE48794B1 (en, 2012) |
| IL (1) | IL57859A (en, 2012) |
| IT (1) | IT1118828B (en, 2012) |
| PH (1) | PH16277A (en, 2012) |
| ZA (1) | ZA794171B (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1170862B (it) * | 1981-03-31 | 1987-06-03 | Sigma Tau Ind Farmaceuti | Mercaptoacil-carnitine procedimento per la loro preparazione e loro uso terapeutico |
| JP3635780B2 (ja) * | 1996-04-08 | 2005-04-06 | 株式会社デンソー | ハニカム構造体の成形装置及び成形方法 |
| CN110597249B (zh) * | 2019-08-23 | 2022-08-05 | 深圳市优必选科技股份有限公司 | 一种机器人及其回充定位方法和装置 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2342142A (en) * | 1937-09-09 | 1944-02-22 | Squibb & Sons Inc | Esters of sulphur-containing benzoic acids and process of preparing them |
| US3328442A (en) * | 1963-12-18 | 1967-06-27 | Massachusetts College Of Pharm | Anti-radiation compounds and their preparation |
| DE2335079C3 (de) * | 1973-02-21 | 1979-02-15 | Laboratories Made S.A., Madrid | Aminoalkylderivate der 3,5-Dimethylbenzoesäure sowie deren Salze und Verfahren zu deren Herstellung |
| US4210666A (en) * | 1978-08-10 | 1980-07-01 | A. H. Robins Company, Inc. | Mucolytic thiophenecarboxamido alkyl mercaptans |
| IL57881A (en) * | 1978-08-10 | 1982-12-31 | Robins Co Inc A H | Pharmaceutical compositions containing benzamidoalkyl merccaptans |
-
1979
- 1979-07-20 IL IL57859A patent/IL57859A/xx unknown
- 1979-08-03 CH CH716879A patent/CH642062A5/fr not_active IP Right Cessation
- 1979-08-03 PH PH22851A patent/PH16277A/en unknown
- 1979-08-08 GB GB7927694A patent/GB2028325B/en not_active Expired
- 1979-08-08 EG EG487/79A patent/EG14416A/xx active
- 1979-08-08 IE IE1520/79A patent/IE48794B1/en unknown
- 1979-08-09 AU AU49756/79A patent/AU520791B2/en not_active Ceased
- 1979-08-09 CA CA333,424A patent/CA1125297A/en not_active Expired
- 1979-08-09 BE BE0/196671A patent/BE878169A/xx not_active IP Right Cessation
- 1979-08-09 DE DE19792932402 patent/DE2932402A1/de active Granted
- 1979-08-09 DK DK333879A patent/DK159655C/da not_active IP Right Cessation
- 1979-08-09 FI FI792474A patent/FI69060C/fi not_active IP Right Cessation
- 1979-08-09 ES ES483269A patent/ES483269A1/es not_active Expired
- 1979-08-09 FR FR7920412A patent/FR2433016A1/fr active Granted
- 1979-08-09 IT IT68643/79A patent/IT1118828B/it active
- 1979-08-10 JP JP10212879A patent/JPS5536486A/ja active Granted
- 1979-08-10 ZA ZA00794171A patent/ZA794171B/xx unknown
-
1980
- 1980-02-14 FR FR8003290A patent/FR2453150A1/fr active Granted
-
1987
- 1987-10-27 JP JP62271595A patent/JPS63119423A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DK333879A (da) | 1980-02-11 |
| BE878169A (fr) | 1979-12-03 |
| FR2453150B1 (en, 2012) | 1983-05-20 |
| IT7968643A0 (it) | 1979-08-09 |
| FR2433016B1 (en, 2012) | 1983-05-13 |
| IT1118828B (it) | 1986-03-03 |
| IE791520L (en) | 1980-02-10 |
| IE48794B1 (en) | 1985-05-15 |
| DE2932402C2 (en, 2012) | 1988-12-22 |
| ZA794171B (en) | 1980-08-27 |
| FI69060B (fi) | 1985-08-30 |
| DK159655C (da) | 1991-04-08 |
| EG14416A (en) | 1984-06-30 |
| FR2453150A1 (fr) | 1980-10-31 |
| DK159655B (da) | 1990-11-12 |
| IL57859A (en) | 1983-02-23 |
| JPS5536486A (en) | 1980-03-14 |
| FR2433016A1 (fr) | 1980-03-07 |
| IL57859A0 (en) | 1979-11-30 |
| JPH0262530B2 (en, 2012) | 1990-12-26 |
| DE2932402A1 (de) | 1980-02-21 |
| AU4975679A (en) | 1980-02-14 |
| CH642062A5 (fr) | 1984-03-30 |
| FI792474A7 (fi) | 1980-02-11 |
| GB2028325A (en) | 1980-03-05 |
| ES483269A1 (es) | 1980-04-16 |
| PH16277A (en) | 1983-08-26 |
| JPS6341899B2 (en, 2012) | 1988-08-19 |
| CA1125297A (en) | 1982-06-08 |
| JPS63119423A (ja) | 1988-05-24 |
| AU520791B2 (en) | 1982-02-25 |
| GB2028325B (en) | 1982-11-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: A.H. ROBINS COMPANY, INCORPORATED |