DE1695910A1 - Verfahren zur Herstellung von neuen an der Aminogruppe substituierten 2-Amino-5-nitro-thiazolen - Google Patents
Verfahren zur Herstellung von neuen an der Aminogruppe substituierten 2-Amino-5-nitro-thiazolenInfo
- Publication number
- DE1695910A1 DE1695910A1 DE19671695910 DE1695910A DE1695910A1 DE 1695910 A1 DE1695910 A1 DE 1695910A1 DE 19671695910 DE19671695910 DE 19671695910 DE 1695910 A DE1695910 A DE 1695910A DE 1695910 A1 DE1695910 A1 DE 1695910A1
- Authority
- DE
- Germany
- Prior art keywords
- nitro
- thiazole
- group
- inorganic
- acid addition
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 7
- 125000003277 amino group Chemical group 0.000 title claims description 3
- MIHADVKEHAFNPG-UHFFFAOYSA-N 2-Amino-5-nitrothiazole Chemical group NC1=NC=C([N+]([O-])=O)S1 MIHADVKEHAFNPG-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 14
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 12
- 150000007524 organic acids Chemical class 0.000 claims description 12
- 235000005985 organic acids Nutrition 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 229960005130 niridazole Drugs 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 150000007522 mineralic acids Chemical class 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
- -1 amino group 2-Amino-5-nitro-thiazoles Chemical class 0.000 claims description 5
- 239000002585 base Substances 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 239000013543 active substance Substances 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 230000000844 anti-bacterial effect Effects 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 230000000507 anthelmentic effect Effects 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 3
- 235000021190 leftovers Nutrition 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
- 230000009257 reactivity Effects 0.000 claims description 3
- 229910052717 sulfur Chemical group 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- RDXLYGJSWZYTFJ-UHFFFAOYSA-N Niridazole Chemical compound S1C([N+](=O)[O-])=CN=C1N1C(=O)NCC1 RDXLYGJSWZYTFJ-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims 2
- 239000003513 alkali Substances 0.000 claims 1
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 238000002844 melting Methods 0.000 description 19
- 230000008018 melting Effects 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
- 239000013078 crystal Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- 235000019359 magnesium stearate Nutrition 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- JLRGRGZKODDLFL-UHFFFAOYSA-N 1,1-bis(methylsulfanyl)-n-(5-nitro-1,3-thiazol-2-yl)methanimine Chemical compound CSC(SC)=NC1=NC=C([N+]([O-])=O)S1 JLRGRGZKODDLFL-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- 229910002012 Aerosil® Inorganic materials 0.000 description 4
- 229920002261 Corn starch Polymers 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000008120 corn starch Substances 0.000 description 4
- 239000008298 dragée Substances 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 229920000159 gelatin Polymers 0.000 description 4
- 235000019322 gelatine Nutrition 0.000 description 4
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 4
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 4
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 4
- 229920001592 potato starch Polymers 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- 239000001828 Gelatine Substances 0.000 description 2
- 235000013871 bee wax Nutrition 0.000 description 2
- 239000012166 beeswax Substances 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 229940031098 ethanolamine Drugs 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- GBAXGHVGQJHFQL-UHFFFAOYSA-N 1-(2-hydroxyethylamino)propan-2-ol Chemical compound CC(O)CNCCO GBAXGHVGQJHFQL-UHFFFAOYSA-N 0.000 description 1
- XNIOWJUQPMKCIJ-UHFFFAOYSA-N 2-(benzylamino)ethanol Chemical compound OCCNCC1=CC=CC=C1 XNIOWJUQPMKCIJ-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-UHFFFAOYSA-N 2-(hydroxymethyl)-6-[4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxane-3,4,5-triol Chemical compound OCC1OC(OC2C(O)C(O)C(O)OC2CO)C(O)C(O)C1O GUBGYTABKSRVRQ-UHFFFAOYSA-N 0.000 description 1
- VVVCJCRUFSIVHI-UHFFFAOYSA-N 5-nitro-1,3-thiazole Chemical compound [O-][N+](=O)C1=CN=CS1 VVVCJCRUFSIVHI-UHFFFAOYSA-N 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 1
- IFKYEXRMYXHBKJ-UHFFFAOYSA-N SC(=NC=1SC=C(N1)[N+](=O)[O-])S Chemical class SC(=NC=1SC=C(N1)[N+](=O)[O-])S IFKYEXRMYXHBKJ-UHFFFAOYSA-N 0.000 description 1
- 101710150115 Sensory rhodopsin-2 Proteins 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- IMIDOCRTMDIQIJ-UHFFFAOYSA-N aminocarb Chemical compound CNC(=O)OC1=CC=C(N(C)C)C(C)=C1 IMIDOCRTMDIQIJ-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 229940102253 isopropanolamine Drugs 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229960003151 mercaptamine Drugs 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D277/58—Nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D277/18—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Washing And Drying Of Tableware (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Priority Applications (19)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL137317D NL137317C (enrdf_load_stackoverflow) | 1967-11-10 | ||
| CH1577167A CH482436A (de) | 1967-11-10 | 1967-11-10 | Automatische, an das Wasserleitungsnetz anschliessbare Geschirrwaschmaschine |
| DE19671695910 DE1695910A1 (de) | 1967-11-10 | 1967-11-16 | Verfahren zur Herstellung von neuen an der Aminogruppe substituierten 2-Amino-5-nitro-thiazolen |
| DE19681800074 DE1800074A1 (de) | 1967-11-10 | 1968-10-01 | Neue 2-[Oxazolidinyliden-(2)-amino]-5-nitrothiazole und Verfahren zu ihrer Herstellung |
| NL6815195A NL6815195A (enrdf_load_stackoverflow) | 1967-11-10 | 1968-10-24 | |
| NL6815915A NL6815915A (enrdf_load_stackoverflow) | 1967-11-10 | 1968-11-08 | |
| BE723590D BE723590A (enrdf_load_stackoverflow) | 1967-11-10 | 1968-11-08 | |
| GB5293968A GB1193728A (en) | 1967-11-10 | 1968-11-08 | Improvements in or relating to Washing Machines |
| CH1692868A CH513196A (de) | 1967-11-10 | 1968-11-13 | Verfahren zur Herstellung von neuen, an der Aminogruppe substituierten 2-Amino-5-nitro-thiazolen |
| BE723940D BE723940A (enrdf_load_stackoverflow) | 1967-11-10 | 1968-11-14 | |
| BR20405868A BR6804058D0 (pt) | 1967-11-16 | 1968-11-14 | Processo para a preparacao de novos a-amino-5-nitro-tiazois substituidos no grupo amino |
| IL31074A IL31074A (en) | 1967-11-16 | 1968-11-15 | 2-amino-5-nitro thiazoles and their preparation |
| AT1115168A AT287706B (de) | 1967-11-16 | 1968-11-15 | Verfahren zur Herstellung von neuen 2-Amino-5-nitrothiazolderivaten und ihren Salzen |
| FR173884A FR8286M (enrdf_load_stackoverflow) | 1967-11-10 | 1968-11-15 | |
| ES360300A ES360300A1 (es) | 1967-11-16 | 1968-11-15 | Procedimiento para la preparacion de nuevos 2-amino-5-nitro-tiazoles sustituidos en el grupo amino. |
| FR1592266D FR1592266A (enrdf_load_stackoverflow) | 1967-11-10 | 1968-11-15 | |
| SE15560/68A SE351219B (enrdf_load_stackoverflow) | 1967-11-16 | 1968-11-15 | |
| GB1250353D GB1250353A (enrdf_load_stackoverflow) | 1967-11-10 | 1968-11-18 | |
| AT321670A AT297697B (de) | 1967-11-16 | 1970-04-08 | Verfahren zur Herstellung des neuen 2-[(4,5,5-Trimethyl-1,3-oxazolidinyliden-(2))-amino]-5-nitrothiazols und seiner Salze |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1577167A CH482436A (de) | 1967-11-10 | 1967-11-10 | Automatische, an das Wasserleitungsnetz anschliessbare Geschirrwaschmaschine |
| DET0035267 | 1967-11-16 | ||
| DE19671695910 DE1695910A1 (de) | 1967-11-10 | 1967-11-16 | Verfahren zur Herstellung von neuen an der Aminogruppe substituierten 2-Amino-5-nitro-thiazolen |
| DE19681800074 DE1800074A1 (de) | 1967-11-10 | 1968-10-01 | Neue 2-[Oxazolidinyliden-(2)-amino]-5-nitrothiazole und Verfahren zu ihrer Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1695910A1 true DE1695910A1 (de) | 1971-05-06 |
Family
ID=27429617
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671695910 Pending DE1695910A1 (de) | 1967-11-10 | 1967-11-16 | Verfahren zur Herstellung von neuen an der Aminogruppe substituierten 2-Amino-5-nitro-thiazolen |
| DE19681800074 Pending DE1800074A1 (de) | 1967-11-10 | 1968-10-01 | Neue 2-[Oxazolidinyliden-(2)-amino]-5-nitrothiazole und Verfahren zu ihrer Herstellung |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681800074 Pending DE1800074A1 (de) | 1967-11-10 | 1968-10-01 | Neue 2-[Oxazolidinyliden-(2)-amino]-5-nitrothiazole und Verfahren zu ihrer Herstellung |
Country Status (6)
| Country | Link |
|---|---|
| BE (2) | BE723590A (enrdf_load_stackoverflow) |
| CH (2) | CH482436A (enrdf_load_stackoverflow) |
| DE (2) | DE1695910A1 (enrdf_load_stackoverflow) |
| FR (2) | FR8286M (enrdf_load_stackoverflow) |
| GB (2) | GB1193728A (enrdf_load_stackoverflow) |
| NL (3) | NL6815195A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0365915A3 (en) * | 1988-10-24 | 1990-08-29 | Bayer Ag | Substituted 2-aminothiazoles |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1918071A1 (de) * | 1969-04-09 | 1970-10-15 | Thomae Gmbh Dr K | 2-[(4,5,5-Trimethyl-1,3-oxazolidinyliden-(2))amino]-5-nitro-thiazol und Verfahren zu seiner Herstellung |
| DE1918070A1 (de) * | 1969-04-09 | 1971-01-21 | Thomae Gmbh Dr K | Neue,an der Aminogruppe substituierte 2-Amino-5-nitro-thiazole und Verfahren zur Herstellung |
| DE1944049A1 (de) * | 1969-08-29 | 1971-03-04 | Thomae Gmbh Dr K | Neue (5-Nitro-2-thiazolyl)-guanidine und Verfahren zur Herstellung |
| DE3220118A1 (de) * | 1982-05-28 | 1983-12-01 | Bayer Ag, 5090 Leverkusen | Alkylenverbrueckte guanidinothiazolderivate, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
-
0
- NL NL137317D patent/NL137317C/xx active
-
1967
- 1967-11-10 CH CH1577167A patent/CH482436A/de not_active IP Right Cessation
- 1967-11-16 DE DE19671695910 patent/DE1695910A1/de active Pending
-
1968
- 1968-10-01 DE DE19681800074 patent/DE1800074A1/de active Pending
- 1968-10-24 NL NL6815195A patent/NL6815195A/xx unknown
- 1968-11-08 GB GB5293968A patent/GB1193728A/en not_active Expired
- 1968-11-08 NL NL6815915A patent/NL6815915A/xx unknown
- 1968-11-08 BE BE723590D patent/BE723590A/xx unknown
- 1968-11-13 CH CH1692868A patent/CH513196A/de not_active IP Right Cessation
- 1968-11-14 BE BE723940D patent/BE723940A/xx unknown
- 1968-11-15 FR FR173884A patent/FR8286M/fr not_active Expired
- 1968-11-15 FR FR1592266D patent/FR1592266A/fr not_active Expired
- 1968-11-18 GB GB1250353D patent/GB1250353A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0365915A3 (en) * | 1988-10-24 | 1990-08-29 | Bayer Ag | Substituted 2-aminothiazoles |
Also Published As
| Publication number | Publication date |
|---|---|
| CH513196A (de) | 1971-09-30 |
| NL6815195A (enrdf_load_stackoverflow) | 1969-05-20 |
| GB1193728A (en) | 1970-06-03 |
| BE723590A (enrdf_load_stackoverflow) | 1969-04-16 |
| FR8286M (enrdf_load_stackoverflow) | 1970-11-09 |
| CH482436A (de) | 1969-12-15 |
| DE1800074A1 (de) | 1970-07-09 |
| BE723940A (enrdf_load_stackoverflow) | 1969-05-16 |
| GB1250353A (enrdf_load_stackoverflow) | 1971-10-20 |
| FR1592266A (enrdf_load_stackoverflow) | 1970-05-11 |
| NL137317C (enrdf_load_stackoverflow) | |
| NL6815915A (enrdf_load_stackoverflow) | 1969-05-13 |
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