SU795462A3 - Способ получени тиокарбамидныхпРОизВОдНыХ - Google Patents
Способ получени тиокарбамидныхпРОизВОдНыХ Download PDFInfo
- Publication number
- SU795462A3 SU795462A3 SU752333906A SU2333906A SU795462A3 SU 795462 A3 SU795462 A3 SU 795462A3 SU 752333906 A SU752333906 A SU 752333906A SU 2333906 A SU2333906 A SU 2333906A SU 795462 A3 SU795462 A3 SU 795462A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- alkyl
- formula
- halogen
- hydrogen
- product
- Prior art date
Links
- 229940042794 thiocarbamide derivative for treatment of tuberculosis Drugs 0.000 title claims abstract description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical class NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 title claims abstract description 4
- 238000000034 method Methods 0.000 title description 5
- 239000000155 melt Substances 0.000 claims abstract description 6
- 150000001412 amines Chemical class 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 230000001430 anti-depressive effect Effects 0.000 abstract 1
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 239000002934 diuretic Substances 0.000 abstract 1
- 230000001882 diuretic effect Effects 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 230000002349 favourable effect Effects 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 150000002540 isothiocyanates Chemical class 0.000 abstract 1
- 231100000053 low toxicity Toxicity 0.000 abstract 1
- 230000000894 saliuretic effect Effects 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 20
- 239000000047 product Substances 0.000 description 18
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 6
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 6
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- -1 1-Phenylbutyl Chemical group 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- IIFVWLUQBAIPMJ-UHFFFAOYSA-N (4-fluorophenyl)methanamine Chemical compound NCC1=CC=C(F)C=C1 IIFVWLUQBAIPMJ-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- LPVNPJMEWWUFHD-UHFFFAOYSA-N 1-fluoro-4-(isothiocyanatomethyl)benzene Chemical compound FC1=CC=C(CN=C=S)C=C1 LPVNPJMEWWUFHD-UHFFFAOYSA-N 0.000 description 1
- SOAHXJQSCRAWRP-UHFFFAOYSA-N 1-isothiocyanatobutylbenzene Chemical compound CCCC(N=C=S)C1=CC=CC=C1 SOAHXJQSCRAWRP-UHFFFAOYSA-N 0.000 description 1
- XHOXKVFLASIOJD-UHFFFAOYSA-N 1-phenylbutan-1-amine Chemical compound CCCC(N)C1=CC=CC=C1 XHOXKVFLASIOJD-UHFFFAOYSA-N 0.000 description 1
- IPSVDERFJPMANL-UHFFFAOYSA-N 2-hydroxyethylthiourea Chemical compound NC(=S)NCCO IPSVDERFJPMANL-UHFFFAOYSA-N 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 235000012907 honey Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- SUKSPZUQUKQLRX-UHFFFAOYSA-N methyl n-[(4-fluorophenyl)methyl]carbamodithioate Chemical compound CSC(=S)NCC1=CC=C(F)C=C1 SUKSPZUQUKQLRX-UHFFFAOYSA-N 0.000 description 1
- PXNQQRIFQYYQFG-UHFFFAOYSA-N n-(1-phenylbutyl)carbamothioyl chloride Chemical compound CCCC(NC(Cl)=S)C1=CC=CC=C1 PXNQQRIFQYYQFG-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/06—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms
- C07C335/10—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
- C07C335/12—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms of an unsaturated carbon skeleton the carbon skeleton containing six-membered aromatic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Pain & Pain Management (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Psychiatry (AREA)
- Cardiology (AREA)
- Rheumatology (AREA)
- Heart & Thoracic Surgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU75GO1303A HU173459B (hu) | 1975-03-14 | 1975-03-14 | Sposob poluchenija novykh proizvodnykh tiomocheviny |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU795462A3 true SU795462A3 (ru) | 1981-01-07 |
Family
ID=10996785
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU752333906A SU795462A3 (ru) | 1975-03-14 | 1975-03-12 | Способ получени тиокарбамидныхпРОизВОдНыХ |
Country Status (18)
| Country | Link |
|---|---|
| AT (1) | AT347476B (fr) |
| BE (1) | BE839502A (fr) |
| CA (1) | CA1069931A (fr) |
| CH (1) | CH619210A5 (fr) |
| CS (1) | CS188132B2 (fr) |
| DD (1) | DD125615A5 (fr) |
| DE (1) | DE2610865A1 (fr) |
| DK (1) | DK107876A (fr) |
| EG (1) | EG12505A (fr) |
| FR (1) | FR2303532A1 (fr) |
| GB (1) | GB1499485A (fr) |
| HU (1) | HU173459B (fr) |
| IL (1) | IL49194A (fr) |
| IN (1) | IN143559B (fr) |
| NL (1) | NL7602670A (fr) |
| PL (1) | PL101310B1 (fr) |
| SE (1) | SE7603242L (fr) |
| SU (1) | SU795462A3 (fr) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU206082B (en) * | 1988-12-23 | 1992-08-28 | Sandoz Ag | Process for producing capsaicin derivatives and pharmaceutical compositions comprising such compounds |
| US6545182B2 (en) * | 2000-04-13 | 2003-04-08 | Allergan Sales, Inc. | Methods and compositions for modulating alpha adrenergic receptor activity |
| US7335803B2 (en) | 2001-10-19 | 2008-02-26 | Allergan, Inc. | Methods and compositions for modulating alpha adrenergic receptor activity |
| US6313172B1 (en) * | 2000-04-13 | 2001-11-06 | Allergan Sales, Inc. | Methods and compositions for modulating alpha adrenergic receptor activity |
| US6534542B2 (en) | 2001-02-27 | 2003-03-18 | Allergen Sales, Inc. | (2-hydroxy)ethyl-thioureas useful as modulators of α2B adrenergic receptors |
| US7276522B2 (en) | 2002-05-21 | 2007-10-02 | Allergan, Inc. | 4-(substituted cycloalkylmethyl) imidazole-2-thiones, 4-(substituted cycloalkenylmethyl) imidazole-2-thiones, 4-(substituted cycloalkylmethyl) imidazol-2-ones, 4-(substituted cycloalkenylmethyl) imidazol-2-ones and related compounds |
| US7358269B2 (en) | 2002-05-21 | 2008-04-15 | Allergan, Inc. | 2-((2-Thioxo-2,3-dihydro-1H-imidazol-4-yl)methyl)-3,4-dihydronapthalen-1(2H)-one |
| US7091232B2 (en) | 2002-05-21 | 2006-08-15 | Allergan, Inc. | 4-(substituted cycloalkylmethyl) imidazole-2-thiones, 4-(substituted cycloalkenylmethyl) imidazole-2-thiones, 4-(substituted cycloalkylmethyl) imidazol-2-ones and 4-(substituted cycloalkenylmethyl) imidazol-2-ones and related compounds |
| US7323485B2 (en) | 2002-05-21 | 2008-01-29 | Allergan, Inc. | 4-(substituted cycloalkylmethyl) imidazole-2-thiones, 4-(substituted cycloalkenylmethyl) imidazole-2-thiones, 4-(substituted cycloalkylmethyl) imidazol-2-ones and 4-(substituted cycloalkenylmethyl) imidazol-2-ones and related compounds |
| BRPI0516025A (pt) | 2004-09-24 | 2008-08-19 | Allergan Sales Inc | 4-(heteroaril-metil e heteroaril-metil substituìda)-imidazol-2-tionas que atuam como agonistas alfa2 adrenérgicos |
| JP2008514601A (ja) | 2004-09-24 | 2008-05-08 | アラーガン、インコーポレイテッド | 特異的α２アドレナリン作動剤としての４−（フェニルメチルおよび置換フェニルメチル）−イミダゾール−２−チオン |
| MX2007003094A (es) | 2004-09-24 | 2007-06-07 | Allergan Inc | 4-(metilo ciclico condensado)-imidazol-2-tionas como agonistas alfa2 adrenergicos. |
| KR101202066B1 (ko) | 2004-09-28 | 2012-11-15 | 알러간, 인코포레이티드 | 특이적인 또는 선택적인 알파2 아드레날린성아고니스트로서 작용하는 비치환된 및 치환된4-벤질-1,3-디히드로-이미다졸-2-티온 및 이를 사용하는방법 |
| US7390829B2 (en) | 2005-06-29 | 2008-06-24 | Allergan, Inc. | Alpha-2 adrenergic agonists |
| US7902247B2 (en) | 2008-01-09 | 2011-03-08 | Allergan, Inc. | Substituted-aryl-2-phenylethyl-1H-imidazole compounds as subtype selective modulators of alpha 2B and/or alpha 2C adrenergic receptors |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB974545A (en) * | 1963-03-14 | 1964-11-04 | Baxter Laboratories Inc | Thioureas |
-
1975
- 1975-03-12 SU SU752333906A patent/SU795462A3/ru active
- 1975-03-14 HU HU75GO1303A patent/HU173459B/hu unknown
-
1976
- 1976-03-10 IL IL49194A patent/IL49194A/xx unknown
- 1976-03-11 CS CS761604A patent/CS188132B2/cs unknown
- 1976-03-12 CH CH307076A patent/CH619210A5/de not_active IP Right Cessation
- 1976-03-12 DK DK107876A patent/DK107876A/da not_active Application Discontinuation
- 1976-03-12 FR FR7607110A patent/FR2303532A1/fr active Granted
- 1976-03-12 CA CA247,778A patent/CA1069931A/fr not_active Expired
- 1976-03-12 AT AT185776A patent/AT347476B/de not_active IP Right Cessation
- 1976-03-12 SE SE7603242A patent/SE7603242L/xx not_active Application Discontinuation
- 1976-03-12 DD DD191816A patent/DD125615A5/xx unknown
- 1976-03-12 BE BE165107A patent/BE839502A/fr unknown
- 1976-03-13 PL PL1976187917A patent/PL101310B1/pl unknown
- 1976-03-14 EG EG152/76A patent/EG12505A/xx active
- 1976-03-15 DE DE19762610865 patent/DE2610865A1/de not_active Withdrawn
- 1976-03-15 GB GB10200/76A patent/GB1499485A/en not_active Expired
- 1976-03-15 NL NL7602670A patent/NL7602670A/xx not_active Application Discontinuation
- 1976-03-15 IN IN456/CAL/1976A patent/IN143559B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK107876A (da) | 1976-09-15 |
| IL49194A (en) | 1980-09-16 |
| IN143559B (fr) | 1977-12-24 |
| DE2610865A1 (de) | 1976-09-30 |
| ATA185776A (de) | 1978-05-15 |
| CS188132B2 (en) | 1979-02-28 |
| HU173459B (hu) | 1979-05-28 |
| SE7603242L (sv) | 1976-10-15 |
| NL7602670A (nl) | 1976-09-16 |
| PL101310B1 (pl) | 1978-12-30 |
| FR2303532B1 (fr) | 1978-12-15 |
| FR2303532A1 (fr) | 1976-10-08 |
| IL49194A0 (en) | 1976-05-31 |
| CH619210A5 (en) | 1980-09-15 |
| GB1499485A (en) | 1978-02-01 |
| CA1069931A (fr) | 1980-01-15 |
| BE839502A (fr) | 1976-07-01 |
| EG12505A (en) | 1980-07-31 |
| DD125615A5 (fr) | 1977-05-04 |
| AT347476B (de) | 1978-12-27 |
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