GB1282535A - (2-IMIDAZOLIN-2-YLAMINO)SUBSTITUTED BENZO[b]THIOPHENES - Google Patents
(2-IMIDAZOLIN-2-YLAMINO)SUBSTITUTED BENZO[b]THIOPHENESInfo
- Publication number
- GB1282535A GB1282535A GB34661/70A GB3466170A GB1282535A GB 1282535 A GB1282535 A GB 1282535A GB 34661/70 A GB34661/70 A GB 34661/70A GB 3466170 A GB3466170 A GB 3466170A GB 1282535 A GB1282535 A GB 1282535A
- Authority
- GB
- United Kingdom
- Prior art keywords
- imidazolin
- ylamino
- chloro
- thiophene
- benzo
- 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
- -1 2-IMIDAZOLIN-2-YLAMINO Chemical class 0.000 title abstract 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 title 1
- 229930192474 thiophene Natural products 0.000 title 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 abstract 6
- 229910021591 Copper(I) chloride Inorganic materials 0.000 abstract 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 abstract 2
- 229940045803 cuprous chloride Drugs 0.000 abstract 2
- 238000006396 nitration reaction Methods 0.000 abstract 2
- 150000002828 nitro derivatives Chemical class 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical class NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 abstract 2
- VJYJBBMMLIDJEF-UHFFFAOYSA-N 1-benzothiophen-2-amine Chemical class C1=CC=C2SC(N)=CC2=C1 VJYJBBMMLIDJEF-UHFFFAOYSA-N 0.000 abstract 1
- ZGILLTVEEBNDOB-UHFFFAOYSA-N 2-chloro-5-nitrobenzonitrile Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(C#N)=C1 ZGILLTVEEBNDOB-UHFFFAOYSA-N 0.000 abstract 1
- NHWQMJMIYICNBP-UHFFFAOYSA-N 2-chlorobenzonitrile Chemical compound ClC1=CC=CC=C1C#N NHWQMJMIYICNBP-UHFFFAOYSA-N 0.000 abstract 1
- QUKCPSYNLDHLNI-UHFFFAOYSA-N 2-nitro-1-benzothiophen-3-amine Chemical class C1=CC=C2C(N)=C([N+]([O-])=O)SC2=C1 QUKCPSYNLDHLNI-UHFFFAOYSA-N 0.000 abstract 1
- STFIRHONXLYBBD-UHFFFAOYSA-N 3-chloro-1-benzothiophen-5-amine Chemical compound NC1=CC=C2SC=C(Cl)C2=C1 STFIRHONXLYBBD-UHFFFAOYSA-N 0.000 abstract 1
- CYYBQONWWYFDTO-UHFFFAOYSA-N 3-chloro-5-nitro-1-benzothiophene Chemical compound ClC=1C2=C(SC1)C=CC(=C2)[N+](=O)[O-] CYYBQONWWYFDTO-UHFFFAOYSA-N 0.000 abstract 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract 1
- 206010020772 Hypertension Diseases 0.000 abstract 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 abstract 1
- 230000021736 acetylation Effects 0.000 abstract 1
- 238000006640 acetylation reaction Methods 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 238000006193 diazotization reaction Methods 0.000 abstract 1
- 125000003963 dichloro group Chemical group Cl* 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 239000012467 final product Substances 0.000 abstract 1
- 230000026030 halogenation Effects 0.000 abstract 1
- 238000005658 halogenation reaction Methods 0.000 abstract 1
- MKIJJIMOAABWGF-UHFFFAOYSA-N methyl 2-sulfanylacetate Chemical compound COC(=O)CS MKIJJIMOAABWGF-UHFFFAOYSA-N 0.000 abstract 1
- WMZGLTDTPSMOMC-UHFFFAOYSA-N methyl 3-amino-5-nitro-1-benzothiophene-2-carboxylate Chemical compound C1=C([N+]([O-])=O)C=C2C(N)=C(C(=O)OC)SC2=C1 WMZGLTDTPSMOMC-UHFFFAOYSA-N 0.000 abstract 1
- WLEJITFJAVPAQY-UHFFFAOYSA-N methyl 3-chloro-5-nitro-1-benzothiophene-2-carboxylate Chemical compound ClC=1C2=C(SC1C(=O)OC)C=CC(=C2)[N+](=O)[O-] WLEJITFJAVPAQY-UHFFFAOYSA-N 0.000 abstract 1
- 230000011987 methylation Effects 0.000 abstract 1
- 238000007069 methylation reaction Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 125000006239 protecting group Chemical group 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 238000010561 standard procedure Methods 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 150000003585 thioureas Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
- C07D333/66—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
- C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D333/70—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1586470A | 1970-03-02 | 1970-03-02 | |
| US20386371A | 1971-12-01 | 1971-12-01 | |
| US00324091A US3808335A (en) | 1970-03-02 | 1973-01-16 | (2-imidazolin-2-ylamino)substituted benzo(b)thiophenes for treating hypertension |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1282535A true GB1282535A (en) | 1972-07-19 |
Family
ID=27360436
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB34661/70A Expired GB1282535A (en) | 1970-03-02 | 1970-07-17 | (2-IMIDAZOLIN-2-YLAMINO)SUBSTITUTED BENZO[b]THIOPHENES |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US3740417A (cg-RX-API-DMAC10.html) |
| BE (1) | BE762726A (cg-RX-API-DMAC10.html) |
| DE (1) | DE2106038C3 (cg-RX-API-DMAC10.html) |
| FR (1) | FR2085659B1 (cg-RX-API-DMAC10.html) |
| GB (1) | GB1282535A (cg-RX-API-DMAC10.html) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5677321A (en) * | 1996-02-29 | 1997-10-14 | Synaptic Pharmaceutical Corporation | 5- and 6-(2-imidazolin-2-ylamino) and -(2-thiazolin-2-ylamino)-benzothiazoles as alpha-2 adrenergic ligands |
| GB2361425A (en) * | 2000-04-17 | 2001-10-24 | Sorex Ltd | Thiourea rodenticide |
| DE102020109429A1 (de) | 2020-04-03 | 2021-10-07 | Arntz Beteiligungs Gmbh & Co. Kg | Antriebsriemen, insbesondere Zahnriemen, mit verbesserten Eigenschaften und Verfahren zur Herstellung hiervon |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH632268A5 (de) * | 1977-01-14 | 1982-09-30 | Sandoz Ag | Verfahren zur herstellung von neuen heterocyclylaminoderivaten. |
| DE69118070T2 (de) * | 1990-09-21 | 1996-11-21 | Sumitomo Chemical Co | Benzofuranyl- und Benzothiophenyl-substituierte Uracilderivate, ihre Herstellung und ihre Verwendung als Herbizide |
| GB9127050D0 (en) * | 1991-12-20 | 1992-02-19 | Orion Yhtymae Oy | Substituted imidazole derivatives and their preparation and use |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1614A (cg-RX-API-DMAC10.html) * | 1903-02-25 |
-
1970
- 1970-07-17 GB GB34661/70A patent/GB1282535A/en not_active Expired
-
1971
- 1971-02-03 FR FR7103594A patent/FR2085659B1/fr not_active Expired
- 1971-02-09 DE DE2106038A patent/DE2106038C3/de not_active Expired
- 1971-02-10 BE BE762726A patent/BE762726A/xx not_active IP Right Cessation
- 1971-12-01 US US00203863A patent/US3740417A/en not_active Expired - Lifetime
-
1973
- 1973-01-16 US US00324091A patent/US3808335A/en not_active Expired - Lifetime
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5677321A (en) * | 1996-02-29 | 1997-10-14 | Synaptic Pharmaceutical Corporation | 5- and 6-(2-imidazolin-2-ylamino) and -(2-thiazolin-2-ylamino)-benzothiazoles as alpha-2 adrenergic ligands |
| US5948804A (en) * | 1996-02-29 | 1999-09-07 | Synaptic Pharmaceutical Corporation | Substituted indoles and uses thereof |
| US6040451A (en) * | 1996-02-29 | 2000-03-21 | Synaptic Pharmaceutical Corporation | Substituted indoles and uses thereof |
| US6159998A (en) * | 1996-02-29 | 2000-12-12 | Synaptic Pharmaceutical Corporation | Substituted indoles and uses thereof |
| US6303643B1 (en) | 1996-02-29 | 2001-10-16 | Synaptic Pharmaceutical Corporation | Substituted indoles and uses thereof |
| US6498177B2 (en) | 1996-02-29 | 2002-12-24 | Synaptic Pharmaceutical Corporation | Indole and benzothiazole derivatives |
| US6723741B2 (en) | 1996-02-29 | 2004-04-20 | Synaptic Pharmaceutical Corporation | Benzimidazoles and benzothiazoles and uses thereof |
| GB2361425A (en) * | 2000-04-17 | 2001-10-24 | Sorex Ltd | Thiourea rodenticide |
| GB2361425B (en) * | 2000-04-17 | 2004-03-31 | Sorex Ltd | Rodenticidal thiourea compounds |
| DE102020109429A1 (de) | 2020-04-03 | 2021-10-07 | Arntz Beteiligungs Gmbh & Co. Kg | Antriebsriemen, insbesondere Zahnriemen, mit verbesserten Eigenschaften und Verfahren zur Herstellung hiervon |
| EP3895881A1 (de) | 2020-04-03 | 2021-10-20 | Arntz Beteiligungs GmbH & Co. KG | Antriebsriemen, insbesondere zahnriemen, mit verbesserten eigenschaften und verfahren zur herstellung hiervon |
Also Published As
| Publication number | Publication date |
|---|---|
| BE762726A (fr) | 1971-08-10 |
| FR2085659B1 (cg-RX-API-DMAC10.html) | 1974-08-30 |
| US3740417A (en) | 1973-06-19 |
| US3808335A (en) | 1974-04-30 |
| DE2106038B2 (de) | 1979-09-27 |
| DE2106038A1 (de) | 1971-09-30 |
| FR2085659A1 (cg-RX-API-DMAC10.html) | 1971-12-31 |
| DE2106038C3 (de) | 1980-06-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |