DE2321786C2 - S↑IV↑ -Benzo-1,2,4-thiadiazine - Google Patents
S↑IV↑ -Benzo-1,2,4-thiadiazineInfo
- Publication number
- DE2321786C2 DE2321786C2 DE2321786A DE2321786A DE2321786C2 DE 2321786 C2 DE2321786 C2 DE 2321786C2 DE 2321786 A DE2321786 A DE 2321786A DE 2321786 A DE2321786 A DE 2321786A DE 2321786 C2 DE2321786 C2 DE 2321786C2
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- benzo
- hydrogen
- atom
- thiadiazines
- 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.)
- Expired
Links
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229960001340 histamine Drugs 0.000 description 6
- XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 6
- 206010006482 Bronchospasm Diseases 0.000 description 5
- 239000000739 antihistaminic agent Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 208000009079 Bronchial Spasm Diseases 0.000 description 4
- 208000014181 Bronchial disease Diseases 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 208000005392 Spasm Diseases 0.000 description 4
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 4
- 229960004373 acetylcholine Drugs 0.000 description 4
- 230000003170 musculotropic effect Effects 0.000 description 4
- 229930008281 A03AD01 - Papaverine Natural products 0.000 description 3
- 208000007101 Muscle Cramp Diseases 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000001078 anti-cholinergic effect Effects 0.000 description 3
- 229960001789 papaverine Drugs 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 208000000884 Airway Obstruction Diseases 0.000 description 2
- 229930003347 Atropine Natural products 0.000 description 2
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 2
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 2
- 230000001387 anti-histamine Effects 0.000 description 2
- 229940065524 anticholinergics inhalants for obstructive airway diseases Drugs 0.000 description 2
- 229940125715 antihistaminic agent Drugs 0.000 description 2
- RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 2
- 229960000396 atropine Drugs 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000000812 cholinergic antagonist Substances 0.000 description 2
- 230000008602 contraction Effects 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 2
- 229960000520 diphenhydramine Drugs 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 229960001361 ipratropium bromide Drugs 0.000 description 2
- KEWHKYJURDBRMN-ZEODDXGYSA-M ipratropium bromide hydrate Chemical compound O.[Br-].O([C@H]1C[C@H]2CC[C@@H](C1)[N@@+]2(C)C(C)C)C(=O)C(CO)C1=CC=CC=C1 KEWHKYJURDBRMN-ZEODDXGYSA-M 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 210000002460 smooth muscle Anatomy 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 230000002048 spasmolytic effect Effects 0.000 description 2
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 2
- RYOOHIUJEJZCFT-UHFFFAOYSA-N 2-[2-(diethylamino)ethylamino]-2-phenylacetic acid 3-methylbutyl ester Chemical compound CCN(CC)CCNC(C(=O)OCCC(C)C)C1=CC=CC=C1 RYOOHIUJEJZCFT-UHFFFAOYSA-N 0.000 description 1
- 206010006440 Bronchial obstruction Diseases 0.000 description 1
- JSQMJXSTVLOQCP-UHFFFAOYSA-N CCCC1=CC=CC2=C1N=C(CN)NS2(C1=CC=CC=C1)=O Chemical compound CCCC1=CC=CC2=C1N=C(CN)NS2(C1=CC=CC=C1)=O JSQMJXSTVLOQCP-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013566 allergen Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003326 anti-histaminergic effect Effects 0.000 description 1
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 1
- 229910001626 barium chloride Inorganic materials 0.000 description 1
- 230000007885 bronchoconstriction Effects 0.000 description 1
- 230000000572 bronchospasmolytic effect Effects 0.000 description 1
- 229960005242 camylofin Drugs 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 210000003630 histaminocyte Anatomy 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003033 spasmogenic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 230000001515 vagal effect Effects 0.000 description 1
- 210000001186 vagus nerve Anatomy 0.000 description 1
- 230000000304 vasodilatating effect Effects 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
- C07D285/15—Six-membered rings
- C07D285/16—Thiadiazines; Hydrogenated thiadiazines
- C07D285/18—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines
- C07D285/20—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems
- C07D285/22—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D285/24—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with oxygen atoms directly attached to the ring sulfur atom
-
- 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
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2321786A DE2321786C2 (de) | 1973-04-30 | 1973-04-30 | S↑IV↑ -Benzo-1,2,4-thiadiazine |
| SE7404375A SE396751B (sv) | 1973-04-30 | 1974-04-01 | Sett att framstella s?72iv-benso-1,2,4-tiadiaziner |
| CH465474A CH586689A5 (enExample) | 1973-04-30 | 1974-04-03 | |
| NL7405029A NL7405029A (enExample) | 1973-04-30 | 1974-04-11 | |
| US05/462,593 US3933805A (en) | 1973-04-30 | 1974-04-22 | S(IV)-benzo-1,2,4-thiadiazine compounds and process for their preparation |
| DK226074A DK134436C (da) | 1973-04-30 | 1974-04-24 | Analogifremgangsmade til fremstilling af s(iv)-benzo-1,2,4-thiadiaziner eller syreadditionssalte deraf |
| JP49046082A JPS5811868B2 (ja) | 1973-04-30 | 1974-04-25 | Ｓ↑１↑ｖ−ベンゾ−１，２，４−チアジアジアジンの製造方法 |
| GB1840874A GB1420560A (en) | 1973-04-30 | 1974-04-26 | S-i-v-benzo-1,2,4-thiadiazines |
| FR7414839A FR2227009B1 (enExample) | 1973-04-30 | 1974-04-29 | |
| BE143788A BE814400A (fr) | 1973-04-30 | 1974-04-30 | Siv-benzo-1 |
| AT356774A AT332419B (de) | 1973-04-30 | 1974-04-30 | Verfahren zur herstellung von neuen s iv-benzo-1,2,4-thiadiazinen und von deren saureadditionssalzen |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2321786A DE2321786C2 (de) | 1973-04-30 | 1973-04-30 | S↑IV↑ -Benzo-1,2,4-thiadiazine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2321786A1 DE2321786A1 (de) | 1974-11-07 |
| DE2321786C2 true DE2321786C2 (de) | 1982-05-27 |
Family
ID=5879683
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2321786A Expired DE2321786C2 (de) | 1973-04-30 | 1973-04-30 | S↑IV↑ -Benzo-1,2,4-thiadiazine |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3933805A (enExample) |
| JP (1) | JPS5811868B2 (enExample) |
| AT (1) | AT332419B (enExample) |
| BE (1) | BE814400A (enExample) |
| CH (1) | CH586689A5 (enExample) |
| DE (1) | DE2321786C2 (enExample) |
| DK (1) | DK134436C (enExample) |
| FR (1) | FR2227009B1 (enExample) |
| GB (1) | GB1420560A (enExample) |
| NL (1) | NL7405029A (enExample) |
| SE (1) | SE396751B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3353853A (en) * | 1965-05-03 | 1967-11-21 | James H Heywood | Tube connecting fastener |
| US4171361A (en) * | 1977-03-31 | 1979-10-16 | Eli Lilly And Company | 1-Substituted-3-amino-6,7-dialkoxy-1H-1,2,4-benzothiadiazine-1-oxides |
| US4100280A (en) * | 1977-08-08 | 1978-07-11 | Eli Lilly And Company | 1,3-Dialkyl-6,7-methoxy-1H-1,2,4-benzothiadiazine-1-oxides |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3287362A (en) * | 1966-11-22 | Substituted j-oxo-j,x-dihydro-l,z,x-benzo- thiadiazine i,i-dioxides and a method for their preparation |
-
1973
- 1973-04-30 DE DE2321786A patent/DE2321786C2/de not_active Expired
-
1974
- 1974-04-01 SE SE7404375A patent/SE396751B/xx unknown
- 1974-04-03 CH CH465474A patent/CH586689A5/xx not_active IP Right Cessation
- 1974-04-11 NL NL7405029A patent/NL7405029A/xx unknown
- 1974-04-22 US US05/462,593 patent/US3933805A/en not_active Expired - Lifetime
- 1974-04-24 DK DK226074A patent/DK134436C/da active
- 1974-04-25 JP JP49046082A patent/JPS5811868B2/ja not_active Expired
- 1974-04-26 GB GB1840874A patent/GB1420560A/en not_active Expired
- 1974-04-29 FR FR7414839A patent/FR2227009B1/fr not_active Expired
- 1974-04-30 AT AT356774A patent/AT332419B/de not_active IP Right Cessation
- 1974-04-30 BE BE143788A patent/BE814400A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK134436C (da) | 1977-04-25 |
| JPS5013384A (enExample) | 1975-02-12 |
| CH586689A5 (enExample) | 1977-04-15 |
| FR2227009A1 (enExample) | 1974-11-22 |
| DK134436B (da) | 1976-11-08 |
| FR2227009B1 (enExample) | 1977-09-09 |
| GB1420560A (en) | 1976-01-07 |
| BE814400A (fr) | 1974-08-16 |
| US3933805A (en) | 1976-01-20 |
| JPS5811868B2 (ja) | 1983-03-04 |
| ATA356774A (de) | 1976-01-15 |
| NL7405029A (enExample) | 1974-11-01 |
| AT332419B (de) | 1976-09-27 |
| DE2321786A1 (de) | 1974-11-07 |
| SE396751B (sv) | 1977-10-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| D2 | Grant after examination | ||
| 8339 | Ceased/non-payment of the annual fee |