NO762821L - - Google Patents
Info
- Publication number
- NO762821L NO762821L NO762821A NO762821A NO762821L NO 762821 L NO762821 L NO 762821L NO 762821 A NO762821 A NO 762821A NO 762821 A NO762821 A NO 762821A NO 762821 L NO762821 L NO 762821L
- Authority
- NO
- Norway
- Prior art keywords
- compounds
- formula
- hydrogen
- stands
- methanol
- Prior art date
Links
- 238000000034 method Methods 0.000 claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- -1 cyano, hydroxy Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 150000002894 organic compounds Chemical class 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LIYJKRDVOXIXCP-UHFFFAOYSA-N [amino(methylsulfanyl)methylidene]-(4-chloro-2,1,3-benzothiadiazol-5-yl)azanium;iodide Chemical compound [I-].ClC1=C([NH+]=C(N)SC)C=CC2=NSN=C21 LIYJKRDVOXIXCP-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 229940093915 gynecological organic acid Drugs 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- QCFGIJDLQHINGA-UHFFFAOYSA-N (4-chloro-2,1,3-benzothiadiazol-5-yl)thiourea Chemical compound ClC1=C(NC(=S)N)C=CC2=NSN=C21 QCFGIJDLQHINGA-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- JRJPKRSKPOCUEV-UHFFFAOYSA-N 2,1,3-benzothiadiazol-5-amine Chemical class C1=C(N)C=CC2=NSN=C21 JRJPKRSKPOCUEV-UHFFFAOYSA-N 0.000 description 1
- JPFOZQOGHFPTOX-UHFFFAOYSA-N 4-bromo-n-(4,5-dihydro-1h-imidazol-2-yl)-2,1,3-benzothiadiazol-5-amine Chemical compound C1=CC2=NSN=C2C(Br)=C1NC1=NCCN1 JPFOZQOGHFPTOX-UHFFFAOYSA-N 0.000 description 1
- RAFNDUBDHJMEDU-UHFFFAOYSA-N 4-chloro-2,1,3-benzothiadiazol-5-amine Chemical compound ClC1=C(N)C=CC2=NSN=C21 RAFNDUBDHJMEDU-UHFFFAOYSA-N 0.000 description 1
- VQAAFLJYBUOSEN-UHFFFAOYSA-N 4-chloro-n-(4,5-dihydro-1h-imidazol-2-yl)-2,1,3-benzothiadiazol-5-amine Chemical compound C1=CC2=NSN=C2C(Cl)=C1NC1=NCCN1 VQAAFLJYBUOSEN-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- JTNYROYIAZZSOG-UHFFFAOYSA-N n-[(4-chloro-2,1,3-benzothiadiazol-5-yl)carbamothioyl]benzamide Chemical compound C1=CC2=NSN=C2C(Cl)=C1NC(=S)NC(=O)C1=CC=CC=C1 JTNYROYIAZZSOG-UHFFFAOYSA-N 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/14—Thiadiazoles; Hydrogenated thiadiazoles condensed with carbocyclic rings or ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pain & Pain Management (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Plural Heterocyclic 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 |
|---|---|---|---|
| CH1091175A CH613966A5 (en) | 1975-08-22 | 1975-08-22 | Process for the preparation of novel 5-(2-imidazolin-2-ylamino)-2,1,3-benzothiadiazoles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO762821L true NO762821L (fr) | 1977-02-23 |
Family
ID=4368128
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO762821A NO762821L (fr) | 1975-08-22 | 1976-08-13 |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS5225774A (fr) |
| AU (1) | AU1707076A (fr) |
| BE (1) | BE845409A (fr) |
| CH (1) | CH613966A5 (fr) |
| DE (1) | DE2636309A1 (fr) |
| DK (1) | DK368376A (fr) |
| ES (1) | ES450875A1 (fr) |
| FI (1) | FI762321A (fr) |
| FR (1) | FR2321287A1 (fr) |
| GB (1) | GB1552163A (fr) |
| IL (1) | IL50324A0 (fr) |
| NL (1) | NL7609156A (fr) |
| NO (1) | NO762821L (fr) |
| NZ (1) | NZ181819A (fr) |
| PT (1) | PT65504B (fr) |
| SE (1) | SE7609085L (fr) |
| YU (1) | YU201976A (fr) |
| ZA (1) | ZA765016B (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4217356A (en) * | 1975-08-22 | 1980-08-12 | Sandoz Ltd. | 2-Imidazolinylamino-2,1,3-benzothiadiazoles |
| JPS54151761U (fr) * | 1978-04-12 | 1979-10-22 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH570401A5 (fr) * | 1972-05-09 | 1975-12-15 | Wander Ag Dr A |
-
1975
- 1975-08-22 CH CH1091175A patent/CH613966A5/xx not_active IP Right Cessation
-
1976
- 1976-08-12 FR FR7624660A patent/FR2321287A1/fr active Granted
- 1976-08-12 DE DE19762636309 patent/DE2636309A1/de not_active Withdrawn
- 1976-08-13 FI FI762321A patent/FI762321A/fi not_active Application Discontinuation
- 1976-08-13 SE SE7609085A patent/SE7609085L/xx unknown
- 1976-08-13 NO NO762821A patent/NO762821L/no unknown
- 1976-08-13 DK DK368376A patent/DK368376A/da unknown
- 1976-08-18 NL NL7609156A patent/NL7609156A/xx not_active Application Discontinuation
- 1976-08-19 YU YU02019/76A patent/YU201976A/xx unknown
- 1976-08-20 ZA ZA00765016A patent/ZA765016B/xx unknown
- 1976-08-20 GB GB34757/76A patent/GB1552163A/en not_active Expired
- 1976-08-20 PT PT65504A patent/PT65504B/fr unknown
- 1976-08-20 IL IL50324A patent/IL50324A0/xx unknown
- 1976-08-20 ES ES450875A patent/ES450875A1/es not_active Expired
- 1976-08-20 BE BE169990A patent/BE845409A/fr not_active IP Right Cessation
- 1976-08-20 JP JP51098843A patent/JPS5225774A/ja active Pending
- 1976-08-20 NZ NZ181819A patent/NZ181819A/xx unknown
- 1976-08-23 AU AU17070/76A patent/AU1707076A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IL50324A0 (en) | 1976-10-31 |
| JPS5225774A (en) | 1977-02-25 |
| GB1552163A (en) | 1979-09-12 |
| NL7609156A (nl) | 1977-02-24 |
| ES450875A1 (es) | 1978-01-01 |
| DE2636309A1 (de) | 1977-03-03 |
| ZA765016B (en) | 1978-03-29 |
| FI762321A (fr) | 1977-02-23 |
| PT65504A (fr) | 1976-09-01 |
| FR2321287A1 (fr) | 1977-03-18 |
| FR2321287B1 (fr) | 1978-11-17 |
| DK368376A (da) | 1977-02-23 |
| NZ181819A (en) | 1978-06-02 |
| YU201976A (en) | 1982-05-31 |
| CH613966A5 (en) | 1979-10-31 |
| SE7609085L (sv) | 1977-02-23 |
| AU1707076A (en) | 1978-03-02 |
| BE845409A (fr) | 1977-02-21 |
| PT65504B (fr) | 1978-05-10 |
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