PL81121B1 - - Google Patents
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- Publication number
- PL81121B1 PL81121B1 PL1970143305A PL14330570A PL81121B1 PL 81121 B1 PL81121 B1 PL 81121B1 PL 1970143305 A PL1970143305 A PL 1970143305A PL 14330570 A PL14330570 A PL 14330570A PL 81121 B1 PL81121 B1 PL 81121B1
- Authority
- PL
- Poland
- Prior art keywords
- acid
- bis
- phenylene
- methyl
- general formula
- Prior art date
Links
- -1 methyl-substituted pyridyl Chemical group 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 7
- PDXWVSDPFXMQGE-UHFFFAOYSA-N [2-(dithiocarboxyamino)phenyl]carbamodithioic acid Chemical class SC(=S)NC1=CC=CC=C1NC(S)=S PDXWVSDPFXMQGE-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 150000001768 cations Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- 125000005493 quinolyl group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 19
- 238000000354 decomposition reaction Methods 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- ABMABYCYRYDRID-UHFFFAOYSA-N [3-(dithiocarboxyamino)phenyl]carbamodithioic acid Chemical compound SC(=S)NC1=CC=CC(NC(S)=S)=C1 ABMABYCYRYDRID-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- GGTIUPJVZZPQKS-UHFFFAOYSA-N [4-(dithiocarboxyamino)phenyl]carbamodithioic acid Chemical compound SC(=S)NC1=CC=C(NC(S)=S)C=C1 GGTIUPJVZZPQKS-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 230000000973 chemotherapeutic effect Effects 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- NJWIMFZLESWFIM-UHFFFAOYSA-N 2-(chloromethyl)pyridine Chemical compound ClCC1=CC=CC=N1 NJWIMFZLESWFIM-UHFFFAOYSA-N 0.000 description 2
- 241001324821 Opisthorchis felineus Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- DTBNVOCQHHLPEH-UHFFFAOYSA-N [4-(dithiocarboxyamino)-2-methylphenyl]carbamodithioic acid Chemical compound CC1=C(C=CC(=C1)NC(S)=S)NC(S)=S DTBNVOCQHHLPEH-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OFPWMRMIFDHXFE-UHFFFAOYSA-N 2-(bromomethyl)pyridine Chemical compound BrCC1=CC=CC=N1 OFPWMRMIFDHXFE-UHFFFAOYSA-N 0.000 description 1
- JPMRGPPMXHGKRO-UHFFFAOYSA-N 2-(chloromethyl)pyridine hydrochloride Chemical compound Cl.ClCC1=CC=CC=N1 JPMRGPPMXHGKRO-UHFFFAOYSA-N 0.000 description 1
- WDETYCRYUBGKCE-UHFFFAOYSA-N 2-(chloromethyl)quinolin-1-ium;chloride Chemical compound Cl.C1=CC=CC2=NC(CCl)=CC=C21 WDETYCRYUBGKCE-UHFFFAOYSA-N 0.000 description 1
- NHXGXNZEADOAJO-UHFFFAOYSA-N 2-(iodomethyl)pyridine Chemical compound ICC1=CC=CC=N1 NHXGXNZEADOAJO-UHFFFAOYSA-N 0.000 description 1
- KHCXGFNZZRXOND-UHFFFAOYSA-N 3-(bromomethyl)pyridine Chemical compound BrCC1=CC=CN=C1 KHCXGFNZZRXOND-UHFFFAOYSA-N 0.000 description 1
- CNQCWYFDIQSALX-UHFFFAOYSA-N 3-(chloromethyl)pyridine Chemical compound ClCC1=CC=CN=C1 CNQCWYFDIQSALX-UHFFFAOYSA-N 0.000 description 1
- DSOGFOBIDOVCHN-UHFFFAOYSA-N 3-(chloromethyl)quinoline Chemical compound C1=CC=CC2=CC(CCl)=CN=C21 DSOGFOBIDOVCHN-UHFFFAOYSA-N 0.000 description 1
- WZIYCIBURCPKAR-UHFFFAOYSA-N 4-(chloromethyl)pyridine Chemical compound ClCC1=CC=NC=C1 WZIYCIBURCPKAR-UHFFFAOYSA-N 0.000 description 1
- OLSKQWRLRYMCAO-UHFFFAOYSA-N 4-(chloromethyl)quinoline Chemical compound C1=CC=C2C(CCl)=CC=NC2=C1 OLSKQWRLRYMCAO-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241001327965 Clonorchis sinensis Species 0.000 description 1
- 241000699800 Cricetinae Species 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- 241000242711 Fasciola hepatica Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 208000006968 Helminthiasis Diseases 0.000 description 1
- 241000699673 Mesocricetus auratus Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000242716 Opisthorchis Species 0.000 description 1
- 241000242541 Trematoda Species 0.000 description 1
- QQZIUNIAUWNAKC-UHFFFAOYSA-N [4-(dithiocarboxyamino)-2,5-dimethylphenyl]carbamodithioic acid Chemical compound CC1=C(C=C(C(=C1)NC(S)=S)C)NC(S)=S QQZIUNIAUWNAKC-UHFFFAOYSA-N 0.000 description 1
- FJXHLSRBMKDMQF-UHFFFAOYSA-N [4-(dithiocarboxyamino)-2-methoxyphenyl]carbamodithioic acid Chemical compound COC1=C(C=CC(=C1)NC(S)=S)NC(S)=S FJXHLSRBMKDMQF-UHFFFAOYSA-N 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 208000006275 fascioliasis Diseases 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 208000014837 parasitic helminthiasis infectious disease Diseases 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/32—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691947746 DE1947746A1 (de) | 1969-09-20 | 1969-09-20 | Phenylen-bis-dithiocarbaminsaeureester und Verfahren zu ihrer Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL81121B1 true PL81121B1 (en, 2012) | 1975-08-30 |
Family
ID=5746104
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1970143305A PL81121B1 (en, 2012) | 1969-09-20 | 1970-09-19 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3676446A (en, 2012) |
| AT (1) | AT299236B (en, 2012) |
| BE (1) | BE756415A (en, 2012) |
| BG (1) | BG18605A3 (en, 2012) |
| CH (1) | CH542844A (en, 2012) |
| CS (1) | CS153562B2 (en, 2012) |
| DE (1) | DE1947746A1 (en, 2012) |
| FR (1) | FR2070080B1 (en, 2012) |
| GB (1) | GB1288828A (en, 2012) |
| NL (1) | NL7013486A (en, 2012) |
| PL (1) | PL81121B1 (en, 2012) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5227492A (en) * | 1988-01-20 | 1993-07-13 | Yamanouchi Pharmaceutical Co., Ltd. | Diurea derivatives useful as medicaments and processes for the preparation thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3308128A (en) * | 1964-01-29 | 1967-03-07 | Searle & Co | Tetrahydro-2-isoquinolylalkyl dithiocarbamates |
| BE692447A (en, 2012) * | 1966-01-13 | 1967-07-11 | ||
| DE1795057A1 (de) * | 1968-08-03 | 1972-01-05 | Hoechst Ag | 1,4-Phenylen-bis-dithiocarbamin-saeureester und Verfahren zu ihrer Herstellung |
| US3579525A (en) * | 1968-10-07 | 1971-05-18 | Stauffer Chemical Co | S-(pyridyl)methyl thio- and dithio-carbamates |
-
0
- BE BE756415D patent/BE756415A/xx unknown
-
1969
- 1969-09-20 DE DE19691947746 patent/DE1947746A1/de active Pending
-
1970
- 1970-08-25 BG BG015538A patent/BG18605A3/xx unknown
- 1970-09-01 CS CS598270A patent/CS153562B2/cs unknown
- 1970-09-08 US US70485A patent/US3676446A/en not_active Expired - Lifetime
- 1970-09-11 NL NL7013486A patent/NL7013486A/xx unknown
- 1970-09-17 CH CH1381370A patent/CH542844A/de not_active IP Right Cessation
- 1970-09-18 AT AT848770A patent/AT299236B/de not_active IP Right Cessation
- 1970-09-19 PL PL1970143305A patent/PL81121B1/pl unknown
- 1970-09-21 GB GB1288828D patent/GB1288828A/en not_active Expired
- 1970-09-21 FR FR7034102A patent/FR2070080B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1947746A1 (de) | 1971-04-08 |
| AT299236B (de) | 1972-06-12 |
| NL7013486A (en, 2012) | 1971-03-23 |
| US3676446A (en) | 1972-07-11 |
| CH542844A (de) | 1973-10-15 |
| FR2070080B1 (en, 2012) | 1973-12-21 |
| BE756415A (fr) | 1971-03-22 |
| CS153562B2 (en, 2012) | 1974-02-25 |
| BG18605A3 (bg) | 1975-02-25 |
| GB1288828A (en, 2012) | 1972-09-13 |
| FR2070080A1 (en, 2012) | 1971-09-10 |
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