DE2133649A1 - Verfahren zur Herstellung von Amino benzthiazolen - Google Patents
Verfahren zur Herstellung von Amino benzthiazolenInfo
- Publication number
- DE2133649A1 DE2133649A1 DE19712133649 DE2133649A DE2133649A1 DE 2133649 A1 DE2133649 A1 DE 2133649A1 DE 19712133649 DE19712133649 DE 19712133649 DE 2133649 A DE2133649 A DE 2133649A DE 2133649 A1 DE2133649 A1 DE 2133649A1
- Authority
- DE
- Germany
- Prior art keywords
- amino
- substituted
- benzothiazole
- substituent
- chemical products
- 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
- UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical class C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 title claims description 29
- 238000000034 method Methods 0.000 title claims description 25
- 239000002904 solvent Substances 0.000 claims description 42
- VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical compound NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 claims description 35
- 238000006243 chemical reaction Methods 0.000 claims description 25
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 20
- -1 aromatic isothiocyanate Chemical class 0.000 claims description 19
- 125000001424 substituent group Chemical class 0.000 claims description 18
- 125000003277 amino group Chemical group 0.000 claims description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 150000007514 bases Chemical class 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 12
- 239000002253 acid Substances 0.000 claims 3
- 239000000376 reactant Substances 0.000 claims 2
- LJAGVJNCLZZNJD-UHFFFAOYSA-N C1(=CC=CC=C1)C=1\S(\C2=C(N=1)C=CC=C2)=N/[H] Chemical group C1(=CC=CC=C1)C=1\S(\C2=C(N=1)C=CC=C2)=N/[H] LJAGVJNCLZZNJD-UHFFFAOYSA-N 0.000 claims 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- 125000006331 halo benzoyl group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical group O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 claims 1
- 239000002798 polar solvent Substances 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 45
- 150000002540 isothiocyanates Chemical class 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 13
- 239000008096 xylene Substances 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 4
- 150000002019 disulfides Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Substances SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- RSPCKAHMRANGJZ-UHFFFAOYSA-N thiohydroxylamine Chemical class SN RSPCKAHMRANGJZ-UHFFFAOYSA-N 0.000 description 3
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001412 amines Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- OMWQUXGVXQELIX-UHFFFAOYSA-N bitoscanate Chemical compound S=C=NC1=CC=C(N=C=S)C=C1 OMWQUXGVXQELIX-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 229940113088 dimethylacetamide Drugs 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical compound S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
- CEBAJHCAFXYWNT-UHFFFAOYSA-N 1-isothiocyanato-4-methylsulfanylbenzene Chemical compound CSC1=CC=C(N=C=S)C=C1 CEBAJHCAFXYWNT-UHFFFAOYSA-N 0.000 description 1
- QLNQINFAKYPRET-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)benzene-1,4-diamine Chemical compound NC1=CC=C(N)C(C=2SC3=CC=CC=C3N=2)=C1 QLNQINFAKYPRET-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- XERMPLQXCQQVGU-UHFFFAOYSA-N 2-amino-3-chlorobenzenethiol Chemical class NC1=C(S)C=CC=C1Cl XERMPLQXCQQVGU-UHFFFAOYSA-N 0.000 description 1
- KKXFKDUISHGLNF-UHFFFAOYSA-N 2-amino-3-methoxybenzenethiol Chemical class COC1=CC=CC(S)=C1N KKXFKDUISHGLNF-UHFFFAOYSA-N 0.000 description 1
- BHEPRJLVZFSHEG-UHFFFAOYSA-N C(C)O.C1=CC=CC=C1.C1=CC=CC=C1 Chemical compound C(C)O.C1=CC=CC=C1.C1=CC=CC=C1 BHEPRJLVZFSHEG-UHFFFAOYSA-N 0.000 description 1
- XJDOEHWHZGFFDM-UHFFFAOYSA-N N=C=S.C1=NC(C=CC=C2)=C2S1 Chemical compound N=C=S.C1=NC(C=CC=C2)=C2S1 XJDOEHWHZGFFDM-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 230000002365 anti-tubercular Effects 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- TXHIDIHEXDFONW-UHFFFAOYSA-N benzene;propan-2-one Chemical compound CC(C)=O.C1=CC=CC=C1 TXHIDIHEXDFONW-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- OCLXJTCGWSSVOE-UHFFFAOYSA-N ethanol etoh Chemical compound CCO.CCO OCLXJTCGWSSVOE-UHFFFAOYSA-N 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 229960005015 local anesthetics Drugs 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229940117953 phenylisothiocyanate Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000003573 thiols Chemical group 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
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
- C07D277/82—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7024954A FR2097405A5 (en) | 1970-07-06 | 1970-07-06 | Benzthiazoles prepn - products useful as eg bactericides and local anaesthetics |
| FR7121070A FR2140862A6 (en) | 1971-06-10 | 1971-06-10 | Benzthiazoles prepn - products useful as eg bactericides and local anaesthetics |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2133649A1 true DE2133649A1 (de) | 1972-01-13 |
Family
ID=26215835
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712133649 Pending DE2133649A1 (de) | 1970-07-06 | 1971-07-06 | Verfahren zur Herstellung von Amino benzthiazolen |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE769490A (enExample) |
| DE (1) | DE2133649A1 (enExample) |
| GB (1) | GB1345552A (enExample) |
| IT (1) | IT1005045B (enExample) |
| LU (1) | LU63457A1 (enExample) |
| NL (1) | NL7109150A (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0912549A4 (en) * | 1996-06-20 | 2002-01-02 | Univ Texas | CONNECTIONS AND METHOD FOR PROVIDING ACTIVE PREPARATIONS AND THE USE THEREOF |
| WO2005070920A1 (en) * | 2004-01-21 | 2005-08-04 | Bristol-Myers Squibb Company | Amino-benzazoles as p2y1 receptor inhibitors |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4826860A (en) * | 1987-03-16 | 1989-05-02 | Warner-Lambert Company | Substituted 2-aminobenzothiazoles and derivatives useful as cerebrovascular agents |
| ES2299504T3 (es) * | 2000-06-21 | 2008-06-01 | F. Hoffmann-La Roche Ag | Derivados de benzotiazol para el tratamiento de la enfermedad de alzheimer y de la enfermedad de parkinson. |
| US7338956B2 (en) * | 2002-08-07 | 2008-03-04 | Sanofi-Aventis Deutschland Gmbh | Acylamino-substituted heteroaromatic compounds and their use as pharmaceuticals |
| US7087761B2 (en) | 2003-01-07 | 2006-08-08 | Hoffmann-La Roche Inc. | Cyclization process for substituted benzothiazole derivatives |
| AU2005247567B2 (en) | 2004-05-24 | 2010-09-02 | F. Hoffmann-La Roche Ag | 4-hydroxy-4-methyl-piperidine-1-carboxylic acid (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amide |
| WO2006048172A1 (en) | 2004-11-05 | 2006-05-11 | F. Hoffmann-La Roche Ag | Process for preparation of isonicotinic acid derivatives |
| AU2006226669B2 (en) | 2005-03-23 | 2011-12-08 | F. Hoffmann-La Roche Ag | Acetylenyl-pyrazolo-pvrimidine derivatives as mGluR2 antagonists |
| BRPI0616571A2 (pt) | 2005-09-27 | 2011-06-21 | Hoffmann La Roche | oxadiazolil pirazol-piridiminas como antagonistas de mglur2, processo para sua preparação, composição farmacêutica que os contém e uso dos mesmo |
| WO2008098851A1 (en) * | 2007-02-14 | 2008-08-21 | Basf Se | Electroluminescent metal complex |
-
1971
- 1971-07-02 LU LU63457D patent/LU63457A1/xx unknown
- 1971-07-02 NL NL7109150A patent/NL7109150A/xx unknown
- 1971-07-05 BE BE769490A patent/BE769490A/xx unknown
- 1971-07-06 DE DE19712133649 patent/DE2133649A1/de active Pending
- 1971-07-06 IT IT4294471A patent/IT1005045B/it active
- 1971-07-06 GB GB3166471A patent/GB1345552A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0912549A4 (en) * | 1996-06-20 | 2002-01-02 | Univ Texas | CONNECTIONS AND METHOD FOR PROVIDING ACTIVE PREPARATIONS AND THE USE THEREOF |
| US6720344B2 (en) | 1996-06-20 | 2004-04-13 | The Board Of Regents Of The University Of Texas System | Methods and compositions for stimulating osteoblast proliferation or treating malignant cell proliferation and methods for selecting osteoblast proliferation stimulants |
| WO2005070920A1 (en) * | 2004-01-21 | 2005-08-04 | Bristol-Myers Squibb Company | Amino-benzazoles as p2y1 receptor inhibitors |
| US7470712B2 (en) | 2004-01-21 | 2008-12-30 | Bristol-Myers Squibb Company | Amino-benzazoles as P2Y1 receptor inhibitors |
| US8053450B2 (en) | 2004-01-21 | 2011-11-08 | Bristol-Myers Squibb Company | Amino-benzazoles as P2Y1 receptor inhibitors with pyridine ring and heterocyclic components |
Also Published As
| Publication number | Publication date |
|---|---|
| IT1005045B (it) | 1976-08-20 |
| GB1345552A (en) | 1974-01-30 |
| BE769490A (fr) | 1971-11-16 |
| NL7109150A (enExample) | 1972-01-10 |
| LU63457A1 (enExample) | 1971-11-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OGA | New person/name/address of the applicant | ||
| OHA | Expiration of time for request for examination |