CA1069931A - Thiocarbamide derivatives and process for preparing thereof - Google Patents

Thiocarbamide derivatives and process for preparing thereof

Info

Publication number: CA1069931A
Authority: CA; Canada
Prior art keywords: group; hydroxyethyl; denotes; thiocarbamide; methyl
Prior art date: 1975-03-14
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

Application number

CA247,778A

Other languages

English (en)

French (fr)

Inventor

Jozsef Reiter

Lajos Toldy

Jozsef Borsi

Inge Schafer

Jozsef Szekely

Ildiko Kiraly

Sandor J. Elek

Eleonora Szondy

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Egyt Gyogyszervegyeszeti Gyar

Original Assignee

Egyt Gyogyszervegyeszeti Gyar

Priority date (The priority date 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 date listed.)

1975-03-14

Filing date

1976-03-12

Publication date

1980-01-15

1976-03-12 Application filed by Egyt Gyogyszervegyeszeti Gyar filed Critical Egyt Gyogyszervegyeszeti Gyar

1980-01-15 Application granted granted Critical

1980-01-15 Publication of CA1069931A publication Critical patent/CA1069931A/en

Status Expired legal-status Critical Current

Links

UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical class NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 title claims abstract description 25
229940042794 thiocarbamide derivative for treatment of tuberculosis Drugs 0.000 title claims abstract description 6
238000004519 manufacturing process Methods 0.000 title 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 45
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims abstract description 42
238000000034 method Methods 0.000 claims abstract description 37
150000001875 compounds Chemical class 0.000 claims abstract description 30
-1 1,1-dimethyl-2-hydroxyethyl group Chemical group 0.000 claims abstract description 26
125000005843 halogen group Chemical group 0.000 claims abstract description 18
125000000217 alkyl group Chemical group 0.000 claims abstract description 16
229920006395 saturated elastomer Polymers 0.000 claims abstract description 12
IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 claims abstract description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
125000004417 unsaturated alkyl group Chemical group 0.000 claims abstract description 7
125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 5
238000002360 preparation method Methods 0.000 claims abstract description 5
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 4
QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims abstract description 4
SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 claims abstract description 4
125000004985 dialkyl amino alkyl group Chemical group 0.000 claims abstract description 4
125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 4
125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract description 4
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims abstract description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
125000006701 (C1-C7) alkyl group Chemical group 0.000 claims abstract 2
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims abstract 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 24
OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 claims description 16
239000012442 inert solvent Substances 0.000 claims description 14
150000001412 amines Chemical class 0.000 claims description 13
239000000155 melt Substances 0.000 claims description 11
239000000126 substance Substances 0.000 claims description 9
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 8
238000002844 melting Methods 0.000 claims description 7
230000008018 melting Effects 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 5
150000002540 isothiocyanates Chemical class 0.000 claims description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
125000003710 aryl alkyl group Chemical group 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
LPVNPJMEWWUFHD-UHFFFAOYSA-N 1-fluoro-4-(isothiocyanatomethyl)benzene Chemical compound FC1=CC=C(CN=C=S)C=C1 LPVNPJMEWWUFHD-UHFFFAOYSA-N 0.000 claims description 2
239000002253 acid Substances 0.000 claims description 2
150000007513 acids Chemical class 0.000 claims description 2
SUKSPZUQUKQLRX-UHFFFAOYSA-N methyl n-[(4-fluorophenyl)methyl]carbamodithioate Chemical compound CSC(=S)NCC1=CC=C(F)C=C1 SUKSPZUQUKQLRX-UHFFFAOYSA-N 0.000 claims description 2
ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims 12
239000001257 hydrogen Substances 0.000 claims 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
150000002431 hydrogen Chemical class 0.000 claims 6
150000003254 radicals Chemical class 0.000 claims 5
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
DEHXIHUIYSXZNH-UHFFFAOYSA-N 1-chloro-4-(isothiocyanatomethyl)benzene Chemical compound ClC1=CC=C(CN=C=S)C=C1 DEHXIHUIYSXZNH-UHFFFAOYSA-N 0.000 claims 2
WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 claims 2
LIMPKEZVOAQSOD-UHFFFAOYSA-N methyl n-[(4-chlorophenyl)methyl]carbamodithioate Chemical compound CSC(=S)NCC1=CC=C(Cl)C=C1 LIMPKEZVOAQSOD-UHFFFAOYSA-N 0.000 claims 2
AHXHRYRWYFSRQJ-UHFFFAOYSA-N 1-(isothiocyanatomethyl)-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(CN=C=S)C=C1 AHXHRYRWYFSRQJ-UHFFFAOYSA-N 0.000 claims 1
HHJNPMOABDDXEL-UHFFFAOYSA-N 1-fluoro-2-(isothiocyanatomethyl)benzene Chemical compound FC1=CC=CC=C1CN=C=S HHJNPMOABDDXEL-UHFFFAOYSA-N 0.000 claims 1
KLNMIWGOGGBFNV-UHFFFAOYSA-N 1-isothiocyanatopropylbenzene Chemical compound S=C=NC(CC)C1=CC=CC=C1 KLNMIWGOGGBFNV-UHFFFAOYSA-N 0.000 claims 1
150000003560 thiocarbamic acids Chemical class 0.000 claims 1
230000000202 analgesic effect Effects 0.000 abstract description 4
230000001430 anti-depressive effect Effects 0.000 abstract description 3
239000002934 diuretic Substances 0.000 abstract description 3
230000001882 diuretic effect Effects 0.000 abstract description 3
230000002349 favourable effect Effects 0.000 abstract description 3
230000000894 saliuretic effect Effects 0.000 abstract description 3
230000000694 effects Effects 0.000 abstract description 2
231100000053 low toxicity Toxicity 0.000 abstract description 2
239000000935 antidepressant agent Substances 0.000 abstract 1
229940005513 antidepressants Drugs 0.000 abstract 1
230000036772 blood pressure Effects 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
239000000203 mixture Substances 0.000 description 13
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 5
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 4
241000699670 Mus sp. Species 0.000 description 4
239000004202 carbamide Substances 0.000 description 4
235000013877 carbamide Nutrition 0.000 description 4
238000001816 cooling Methods 0.000 description 4
IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 4
238000003756 stirring Methods 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
238000004821 distillation Methods 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
239000002904 solvent Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
230000004531 blood pressure lowering effect Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
GNVMUORYQLCPJZ-UHFFFAOYSA-N carbamothioic s-acid Chemical compound NC(S)=O GNVMUORYQLCPJZ-UHFFFAOYSA-N 0.000 description 2
BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
IIFVWLUQBAIPMJ-UHFFFAOYSA-N (4-fluorophenyl)methanamine Chemical compound NCC1=CC=C(F)C=C1 IIFVWLUQBAIPMJ-UHFFFAOYSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 1
125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 description 1
125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 description 1
125000006494 2-trifluoromethyl benzyl group Chemical group [H]C1=C([H])C([H])=C(C(=C1[H])C([H])([H])*)C(F)(F)F 0.000 description 1
AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 description 1
ZQSCNOCLGUTXNV-UHFFFAOYSA-N 2h-thiazocine Chemical class C1=CC=CSNC=C1 ZQSCNOCLGUTXNV-UHFFFAOYSA-N 0.000 description 1
125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 description 1
125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 description 1
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 description 1
125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 1
125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001318 4-trifluoromethylbenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(F)(F)F 0.000 description 1
RMMXTBMQSGEXHJ-UHFFFAOYSA-N Aminophenazone Chemical compound O=C1C(N(C)C)=C(C)N(C)N1C1=CC=CC=C1 RMMXTBMQSGEXHJ-UHFFFAOYSA-N 0.000 description 1
RRXSYZFVDIRTFB-UHFFFAOYSA-N C[CH]C1=CC=C(OC)C=C1 Chemical group C[CH]C1=CC=C(OC)C=C1 RRXSYZFVDIRTFB-UHFFFAOYSA-N 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
229960000212 aminophenazone Drugs 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
244000309464 bull Species 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
229950005499 carbon tetrachloride Drugs 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
XLMALTXPSGQGBX-GCJKJVERSA-N dextropropoxyphene Chemical compound C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 XLMALTXPSGQGBX-GCJKJVERSA-N 0.000 description 1
229960004193 dextropropoxyphene Drugs 0.000 description 1
125000006286 dichlorobenzyl group Chemical group 0.000 description 1
239000012990 dithiocarbamate Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
235000012907 honey Nutrition 0.000 description 1
230000002045 lasting effect Effects 0.000 description 1
125000006178 methyl benzyl group Chemical group 0.000 description 1
229960005181 morphine Drugs 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
229960003147 reserpine Drugs 0.000 description 1
MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
NYERMPLPURRVGM-UHFFFAOYSA-N thiazepine Chemical compound S1C=CC=CC=N1 NYERMPLPURRVGM-UHFFFAOYSA-N 0.000 description 1
CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 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)

CA247,778A 1975-03-14 1976-03-12 Thiocarbamide derivatives and process for preparing thereof Expired CA1069931A (en)

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
CA1069931A true CA1069931A (en)	1980-01-15

Family

ID=10996785

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA247,778A Expired CA1069931A (en)	1975-03-14	1976-03-12	Thiocarbamide derivatives and process for preparing thereof

Country Status (18)

Country	Link
AT (1)	AT347476B (de)
BE (1)	BE839502A (de)
CA (1)	CA1069931A (de)
CH (1)	CH619210A5 (de)
CS (1)	CS188132B2 (de)
DD (1)	DD125615A5 (de)
DE (1)	DE2610865A1 (de)
DK (1)	DK107876A (de)
EG (1)	EG12505A (de)
FR (1)	FR2303532A1 (de)
GB (1)	GB1499485A (de)
HU (1)	HU173459B (de)
IL (1)	IL49194A (de)
IN (1)	IN143559B (de)
NL (1)	NL7602670A (de)
PL (1)	PL101310B1 (de)
SE (1)	SE7603242L (de)
SU (1)	SU795462A3 (de)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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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 DD DD191816A patent/DD125615A5/xx unknown
- 1976-03-12 DK DK107876A patent/DK107876A/da not_active Application Discontinuation
- 1976-03-12 BE BE165107A patent/BE839502A/xx unknown
- 1976-03-12 CA CA247,778A patent/CA1069931A/en not_active Expired
- 1976-03-12 FR FR7607110A patent/FR2303532A1/fr active Granted
- 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 CH CH307076A patent/CH619210A5/de not_active IP Right Cessation
- 1976-03-13 PL PL1976187917A patent/PL101310B1/pl unknown
- 1976-03-14 EG EG152/76A patent/EG12505A/xx active
- 1976-03-15 GB GB10200/76A patent/GB1499485A/en not_active Expired
- 1976-03-15 DE DE19762610865 patent/DE2610865A1/de not_active Withdrawn
- 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
DD125615A5 (de)	1977-05-04
NL7602670A (nl)	1976-09-16
IL49194A0 (en)	1976-05-31
GB1499485A (en)	1978-02-01
EG12505A (en)	1980-07-31
AT347476B (de)	1978-12-27
PL101310B1 (pl)	1978-12-30
IL49194A (en)	1980-09-16
SU795462A3 (ru)	1981-01-07
HU173459B (hu)	1979-05-28
ATA185776A (de)	1978-05-15
DE2610865A1 (de)	1976-09-30
CS188132B2 (en)	1979-02-28
FR2303532B1 (de)	1978-12-15
SE7603242L (sv)	1976-10-15
FR2303532A1 (fr)	1976-10-08
CH619210A5 (en)	1980-09-15
BE839502A (fr)	1976-07-01
IN143559B (de)	1977-12-24
DK107876A (da)	1976-09-15

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AU661276B2 (en)	1995-07-20	Piperidine compounds, their preparation and use
US2940969A (en)	1960-06-14	1-substituted-4-[3-(9-xanthylidene)-propyl] piperazines and 1-substituted-4-[3-(10-thiaxanthylidene) propyl]-piperazines
US4061647A (en)	1977-12-06	Thiazolidine derivatives
NO125183B (de)	1972-07-31
US3200151A (en)	1965-08-10	Arylaminoalkyl guanidines
EP0130224B1 (de)	1986-09-10	Verfahren zur Herstellung von 2-Amino-3,5-dibrombenzylaminen
DE68924221T2 (de)	1996-02-15	Imidazolderivate.
PL109995B1 (en)	1980-06-30	Method of producing derivatives of 4-/n-acetylo/aminotetrahydro-1,3,5-triazynodione-2,6
US4009166A (en)	1977-02-22	Pyrido(2,3-d) pyrimidinones
HU196955B (en)	1989-02-28	Process for producing substituted phenyl-hydrazine derivatives
NO803160L (no)	1978-08-07	Pyrimidin-derivater.
PL129275B1 (en)	1984-04-30	Process for preparing 1-amino-1,3,5-triazine-2,4/1h,3h/-diones
US2783240A (en)	1957-02-26	Heterocyclic sulfonamides
EA035946B1 (ru)	2020-09-04	Способ получения гидрохлоридов 2-(гомо)пиперазин-1,3-бензотиазин-4-она
US4720549A (en)	1988-01-19	Process for the preparation of imidazolyl-methane derivatives
DE10353205A1 (de)	2005-06-16	Ortho-substituierte Pentafluorsulfuranyl-Benzole, Verfahren zu ihrer Herstellung sowie ihre Verwendung als wertvolle Synthese-Zwischenstufen
US1866956A (en)	1932-07-12	Phenyl-indol-sulphonic acids
SU1246890A3 (ru)	1986-07-23	Способ получени производных алкилендиамина,их смесей,рацематов или солей
IL45970A (en)	1977-08-31	3-(4-pyridyl-2-thiazolyl)urea and thiourea derivatives their preparation and pharmaceutical compositions containing them
KR20060037436A (ko)	2006-05-03	Ｎｐｙ 길항물질로서 싸이아졸 유도체

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1997-01-15	MKEX	Expiry