CA1125297A - Benzene and thiophene-carbothioic acid 2-aminoalkyl ester acid salts - Google Patents
Benzene and thiophene-carbothioic acid 2-aminoalkyl ester acid saltsInfo
- Publication number
- CA1125297A CA1125297A CA333,424A CA333424A CA1125297A CA 1125297 A CA1125297 A CA 1125297A CA 333424 A CA333424 A CA 333424A CA 1125297 A CA1125297 A CA 1125297A
- Authority
- CA
- Canada
- Prior art keywords
- acid
- chloride
- thiophene
- aminoethyl ester
- benzene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 title claims abstract description 41
- 239000002253 acid Substances 0.000 title claims abstract description 21
- JOCRHSHXHVVIFS-UHFFFAOYSA-N thiophene-2-carbothioic s-acid Chemical compound SC(=O)C1=CC=CS1 JOCRHSHXHVVIFS-UHFFFAOYSA-N 0.000 title claims abstract description 6
- 150000003839 salts Chemical class 0.000 title claims abstract description 5
- 238000000034 method Methods 0.000 claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 16
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052801 chlorine Inorganic materials 0.000 claims abstract 3
- 239000000460 chlorine Substances 0.000 claims abstract 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 18
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 15
- 150000002148 esters Chemical class 0.000 claims description 13
- OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical compound Cl.NCCS OGMADIBCHLQMIP-UHFFFAOYSA-N 0.000 claims description 7
- 150000001555 benzenes Chemical class 0.000 claims description 5
- LBVWMBBKFFQMRX-UHFFFAOYSA-N 4-chlorobenzenecarbothioic s-acid Chemical compound SC(=O)C1=CC=C(Cl)C=C1 LBVWMBBKFFQMRX-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- MXMOTZIXVICDSD-UHFFFAOYSA-N anisoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1 MXMOTZIXVICDSD-UHFFFAOYSA-N 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 claims description 2
- NQUVCRCCRXRJCK-UHFFFAOYSA-N 4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1 NQUVCRCCRXRJCK-UHFFFAOYSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 5
- YGAPOICUMNPIPF-UHFFFAOYSA-N 4-methoxybenzenecarbothioic s-acid Chemical compound COC1=CC=C(C(S)=O)C=C1 YGAPOICUMNPIPF-UHFFFAOYSA-N 0.000 claims 2
- PJHWTWHVCOZCPU-UHFFFAOYSA-N 4-methylbenzenecarbothioic s-acid Chemical compound CC1=CC=C(C(O)=S)C=C1 PJHWTWHVCOZCPU-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- QIQITDHWZYEEPA-UHFFFAOYSA-N thiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CS1 QIQITDHWZYEEPA-UHFFFAOYSA-N 0.000 claims 1
- 241001465754 Metazoa Species 0.000 abstract description 6
- 210000003097 mucus Anatomy 0.000 abstract description 5
- 230000001747 exhibiting effect Effects 0.000 abstract description 2
- 206010037368 Pulmonary congestion Diseases 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
- -1 2-aminoethyl ester Chemical class 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 210000002784 stomach Anatomy 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000000510 mucolytic effect Effects 0.000 description 5
- 210000004072 lung Anatomy 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000003172 expectorant agent Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 3
- 229940066491 mucolytics Drugs 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- ATADHKWKHYVBTJ-UHFFFAOYSA-N hydron;4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol;chloride Chemical compound Cl.CNCC(O)C1=CC=C(O)C(O)=C1 ATADHKWKHYVBTJ-UHFFFAOYSA-N 0.000 description 2
- 230000002101 lytic effect Effects 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000001665 trituration Methods 0.000 description 2
- NSMXQKNUPPXBRG-SECBINFHSA-N (R)-lisofylline Chemical compound O=C1N(CCCC[C@H](O)C)C(=O)N(C)C2=C1N(C)C=N2 NSMXQKNUPPXBRG-SECBINFHSA-N 0.000 description 1
- GNETVHIDZPYGGD-UHFFFAOYSA-N 1-aminoethanethiol;hydrochloride Chemical compound Cl.CC(N)S GNETVHIDZPYGGD-UHFFFAOYSA-N 0.000 description 1
- OVVJBTKDAFOUBY-UHFFFAOYSA-N 3,4-dichlorobenzenecarbothioic s-acid Chemical compound SC(=O)C1=CC=C(Cl)C(Cl)=C1 OVVJBTKDAFOUBY-UHFFFAOYSA-N 0.000 description 1
- RGAKSNQOIIYQRM-UHFFFAOYSA-N 3,4-dimethylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1C RGAKSNQOIIYQRM-UHFFFAOYSA-N 0.000 description 1
- OQVKGSDRYMYQKF-UHFFFAOYSA-N 3-(trifluoromethyl)benzenecarbothioic s-acid Chemical compound OC(=S)C1=CC=CC(C(F)(F)F)=C1 OQVKGSDRYMYQKF-UHFFFAOYSA-N 0.000 description 1
- RUJYJCANMOTJMO-UHFFFAOYSA-N 3-(trifluoromethyl)benzoyl chloride Chemical compound FC(F)(F)C1=CC=CC(C(Cl)=O)=C1 RUJYJCANMOTJMO-UHFFFAOYSA-N 0.000 description 1
- GMEDUXHKSSWXSL-UHFFFAOYSA-N 3-sulfanylpropylazanium;chloride Chemical compound Cl.NCCCS GMEDUXHKSSWXSL-UHFFFAOYSA-N 0.000 description 1
- CZKLEJHVLCMVQR-UHFFFAOYSA-N 4-fluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C=C1 CZKLEJHVLCMVQR-UHFFFAOYSA-N 0.000 description 1
- TXTGBKDPANLZJK-UHFFFAOYSA-N 4-sulfanylcarbonylbenzoic acid Chemical compound OC(=O)C1=CC=C(C(O)=S)C=C1 TXTGBKDPANLZJK-UHFFFAOYSA-N 0.000 description 1
- 206010011732 Cyst Diseases 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 description 1
- 244000228957 Ferula foetida Species 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
- 240000000233 Melia azedarach Species 0.000 description 1
- 102000001621 Mucoproteins Human genes 0.000 description 1
- 108010093825 Mucoproteins Proteins 0.000 description 1
- 241001201614 Prays Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 208000031513 cyst Diseases 0.000 description 1
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 230000002550 fecal effect Effects 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 230000000762 glandular Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000011777 magnesium Substances 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
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- KRTSDMXIXPKRQR-AATRIKPKSA-N monocrotophos Chemical compound CNC(=O)\C=C(/C)OP(=O)(OC)OC KRTSDMXIXPKRQR-AATRIKPKSA-N 0.000 description 1
- 239000006199 nebulizer Substances 0.000 description 1
- MWLJXOBIPFZRSL-UHFFFAOYSA-N o-(2-aminoethyl) benzenecarbothioate Chemical compound NCCOC(=S)C1=CC=CC=C1 MWLJXOBIPFZRSL-UHFFFAOYSA-N 0.000 description 1
- SGLFZCDLENYTQD-UHFFFAOYSA-N o-(3-aminopropyl) benzenecarbothioate Chemical compound NCCCOC(=S)C1=CC=CC=C1 SGLFZCDLENYTQD-UHFFFAOYSA-N 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010792 warming 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)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (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)
- Bioinformatics & Cheminformatics (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)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA396,307A CA1134273A (en) | 1978-08-10 | 1982-02-15 | Benzene and thiophene-carbothioic acid 2-aminoalkyl ester acid salts |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US93274778A | 1978-08-10 | 1978-08-10 | |
| US932,747 | 1978-08-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1125297A true CA1125297A (en) | 1982-06-08 |
Family
ID=25462846
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA333,424A Expired CA1125297A (en) | 1978-08-10 | 1979-08-09 | Benzene and thiophene-carbothioic acid 2-aminoalkyl ester acid salts |
Country Status (17)
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 IE IE1520/79A patent/IE48794B1/en unknown
- 1979-08-08 GB GB7927694A patent/GB2028325B/en not_active Expired
- 1979-08-08 EG EG487/79A patent/EG14416A/xx active
- 1979-08-09 FR FR7920412A patent/FR2433016A1/fr active Granted
- 1979-08-09 DE DE19792932402 patent/DE2932402A1/de active Granted
- 1979-08-09 ES ES483269A patent/ES483269A1/es not_active Expired
- 1979-08-09 CA CA333,424A patent/CA1125297A/en not_active Expired
- 1979-08-09 AU AU49756/79A patent/AU520791B2/en not_active Ceased
- 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 IT IT68643/79A patent/IT1118828B/it active
- 1979-08-09 BE BE0/196671A patent/BE878169A/xx not_active IP Right Cessation
- 1979-08-10 ZA ZA00794171A patent/ZA794171B/xx unknown
- 1979-08-10 JP JP10212879A patent/JPS5536486A/ja active Granted
-
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
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SU820659A3 (ru) | Способ получени производных 4-амино- 5-АлКилСульфОНилОАНизАМидОВ, иХ СОлЕй,ОКиСЕй, лЕВО- и пРАВОВРАщАющиХизОМЕРОВ /иХ ВАРиАНТы/ | |
| US5571810A (en) | Thiophene derivatives | |
| CA2609659A1 (en) | Azanaphthalenes, compositions and methods for treating retinal disease | |
| DK159264B (da) | Analogifremgangsmaade til fremstilling af d-(threo)-1-aryl-2-acylamido-3-fluor-1-propanolforbindelser | |
| WO1999052525A1 (es) | Tienilazolilalcoxietanaminas, su preparacion y su aplicacion como medicamentos | |
| CY1522A (en) | 1-pyrimidinyloxy-3-hetarylalkylamino-2-propanols preparation and uses | |
| DE3419009A1 (de) | Neue substituierte bis(4-aminophenyl)sulfone, ihre herstellung und ihre verwendung als arzneimittel | |
| CA1125297A (en) | Benzene and thiophene-carbothioic acid 2-aminoalkyl ester acid salts | |
| JP3226920B2 (ja) | １，２−ジチオール−３−チオン誘導体に基づく治療組成物 | |
| EP0125636A1 (de) | Pyridazinone, ihre Herstellung und Verwendung, Pyridazinone enthaltende Arzneimittel | |
| EP0592664B1 (en) | Derivatives of diphenylthiazole with antiinflammatory activity | |
| JP3045354B2 (ja) | チオキサンテノン類およびその抗腫瘍剤 | |
| CA1095055A (en) | Benzamidine derivatives, process for their preparation and applications thereof | |
| US4112106A (en) | N-(2-thiazolyl)-tetrazole-5-carboxamide derivatives for the prevention of immediate type hypersensitivity reactions | |
| US4159380A (en) | Imidazolylethoxy derivatives of pyrazolo[3,4-b]pyridine-5-methanols | |
| NL8803092A (nl) | Tromethaminezout van 1-methyl-beta-oxo-alfa-(fenylcarbamoyl)-2-pyrroolpropionitril. | |
| SU784763A3 (ru) | Способ получени производных 6- метокси-2-ацетилнафтилоксима или их хлоргидратов | |
| GB2290786A (en) | Quinoline derivatives | |
| CN102600164B (zh) | 嘧啶醚类化合物作为制备抗肿瘤药物的应用 | |
| ES2253315T3 (es) | Analogos de fenoxacina para el tratamiento de amiloides. | |
| EP0143001B1 (en) | Pyrimidoisoquinoline derivatives | |
| US4296092A (en) | Mucolytic benzene and thiophene-carbothioic acid 2-aminoalkyl ester acid salts | |
| CA1134273A (en) | Benzene and thiophene-carbothioic acid 2-aminoalkyl ester acid salts | |
| WO1993025520A1 (en) | 5-amino-2-phenoxysulfonanilide compound | |
| CH655095A5 (it) | 2-metossifenil esteri di aminoacidi n-sostituiti, procedimento per la loro preparazione e composizioni farmaceutiche che li contengono. |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |