CY1485A - Benzothienylallylamines process for their production and their use as pharmaceuticals - Google Patents
Benzothienylallylamines process for their production and their use as pharmaceuticals Download PDFInfo
- Publication number
- CY1485A CY1485A CY1485A CY148589A CY1485A CY 1485 A CY1485 A CY 1485A CY 1485 A CY1485 A CY 1485A CY 148589 A CY148589 A CY 148589A CY 1485 A CY1485 A CY 1485A
- Authority
- CY
- Cyprus
- Prior art keywords
- compound
- formula
- acid addition
- free base
- addition salt
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 239000003814 drug Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 57
- 239000000203 mixture Substances 0.000 claims description 32
- 239000002253 acid Substances 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 239000012458 free base Substances 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- -1 cyano, formyl Chemical group 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 208000015181 infectious disease Diseases 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 230000001857 anti-mycotic effect Effects 0.000 claims description 3
- 230000000973 chemotherapeutic effect Effects 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 239000002543 antimycotic Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- HTGDXVFSLALAAZ-FNORWQNLSA-N (e)-n-[(3-chloro-1-benzothiophen-7-yl)methyl]-n,6,6-trimethylhept-2-en-4-yn-1-amine Chemical compound CC(C)(C)C#C/C=C/CN(C)CC1=CC=CC2=C1SC=C2Cl HTGDXVFSLALAAZ-FNORWQNLSA-N 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
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- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 22
- 239000012074 organic phase Substances 0.000 description 20
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 13
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
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- 229910002027 silica gel Inorganic materials 0.000 description 11
- 229960001866 silicon dioxide Drugs 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
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- 229910052801 chlorine Inorganic materials 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 239000011261 inert gas Substances 0.000 description 7
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- 230000000694 effects Effects 0.000 description 6
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- 229910052794 bromium Inorganic materials 0.000 description 4
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- 241000222120 Candida <Saccharomycetales> Species 0.000 description 3
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- 229960000583 acetic acid Drugs 0.000 description 3
- 229940093499 ethyl acetate Drugs 0.000 description 3
- 235000019439 ethyl acetate Nutrition 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 description 3
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- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 208000002474 Tinea Diseases 0.000 description 1
- 241000223238 Trichophyton Species 0.000 description 1
- 206010067409 Trichophytosis Diseases 0.000 description 1
- JQXOYPAIPQCIDF-UHFFFAOYSA-N [7-(methylaminomethyl)-1-benzothiophen-3-yl]methanol Chemical compound CNCC1=CC=CC2=C1SC=C2CO JQXOYPAIPQCIDF-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- PMOWTIHVNWZYFI-WAYWQWQTSA-N cis-2-coumaric acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1O PMOWTIHVNWZYFI-WAYWQWQTSA-N 0.000 description 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 230000037304 dermatophytes Effects 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-M fumarate(1-) Chemical compound OC(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-M 0.000 description 1
- 208000024386 fungal infectious disease Diseases 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000005905 mesyloxy group Chemical group 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 1
- QOCPNIYDGRIJEW-UHFFFAOYSA-N n-(1-benzothiophen-7-ylmethyl)-n,6,6-trimethylhept-2-en-4-yn-1-amine Chemical compound CC(C)(C)C#CC=CCN(C)CC1=CC=CC2=C1SC=C2 QOCPNIYDGRIJEW-UHFFFAOYSA-N 0.000 description 1
- BLCXVOKJOLMUJS-UHFFFAOYSA-N n-methyl-1-(2-methylsulfanyl-1-benzothiophen-7-yl)methanamine Chemical compound CNCC1=CC=CC2=C1SC(SC)=C2 BLCXVOKJOLMUJS-UHFFFAOYSA-N 0.000 description 1
- YUODRWQOGSXMEU-UHFFFAOYSA-N n-methyl-1-(3-methyl-1-benzothiophen-7-yl)methanamine Chemical compound CNCC1=CC=CC2=C1SC=C2C YUODRWQOGSXMEU-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- UYCAUPASBSROMS-UHFFFAOYSA-M sodium;2,2,2-trifluoroacetate Chemical compound [Na+].[O-]C(=O)C(F)(F)F UYCAUPASBSROMS-UHFFFAOYSA-M 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
- C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
- C07C29/40—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing carbon-to-metal bonds
-
- 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
- C07D333/56—Radicals substituted by oxygen atoms
-
- 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
- C07D333/58—Radicals substituted by nitrogen atoms
-
- 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
- C07D333/60—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heat-Exchange Devices With Radiators And Conduit Assemblies (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Refuge Islands, Traffic Blockers, Or Guard Fence (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH656/82A CH653028A5 (de) | 1982-02-03 | 1982-02-03 | Benzthiophenallylamin-verbindungen und verfahren zu ihrer herstellung. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CY1485A true CY1485A (en) | 1989-12-08 |
Family
ID=4192086
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CY1485A CY1485A (en) | 1982-02-03 | 1989-12-08 | Benzothienylallylamines process for their production and their use as pharmaceuticals |
Country Status (28)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH672311A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1985-09-14 | 1989-11-15 | Sandoz Ag | |
| US5068359A (en) * | 1989-06-20 | 1991-11-26 | Ciba-Geigy Corporation | Microbicidal compositions |
| CA2038633A1 (en) * | 1990-03-20 | 1991-09-21 | Yoshimi Tsuchiya | Substituted amine derivatives having anti-hyperlipemia activity |
| FR2695930B1 (fr) * | 1992-09-22 | 1994-12-23 | Sanofi Elf | Dérivé du 2-éthyl benzo[b]thiophène, son procédé de préparation et son utilisation comme intermédiaire de synthèse. |
| JP4759500B2 (ja) * | 2001-02-22 | 2011-08-31 | 帝人株式会社 | ベンゾ［ｂ］チオフェン誘導体、およびその製造方法 |
| CA2627489A1 (en) * | 2005-10-27 | 2007-05-03 | Teijin Pharma Limited | Benzo[b]thiophen derivative and process for their production |
| CN102898314B (zh) * | 2012-11-13 | 2014-09-03 | 山东铂源药业有限公司 | 一种盐酸特比萘芬的制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1250019B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1963-07-19 | |||
| CH442353A (de) * | 1964-04-16 | 1967-08-31 | Sandoz Ag | Verfahren zur Herstellung von neuen Benzothiophen-Derivaten |
| US3930537A (en) * | 1974-05-06 | 1976-01-06 | The United States Of America As Represented By The United States Energy Research And Development Administration | Heat exchanger |
| EP0000896B1 (en) * | 1977-08-19 | 1982-10-13 | Sandoz Ag | Propenyl amines, processes for their production and pharmaceutical compositions containing them |
| DE19375084I2 (de) * | 1979-08-22 | 2000-11-16 | Novartis Ag | Propenylamine Verfahren zu ihrer Herstellung sie enthaltende pharmazeutische Zusammensetzungen und ihre Verwendung als Arzneimittel |
-
1982
- 1982-02-03 CH CH656/82A patent/CH653028A5/de not_active IP Right Cessation
-
1983
- 1983-01-25 US US06/460,782 patent/US4474141A/en not_active Expired - Lifetime
- 1983-01-27 FI FI830297A patent/FI80689C/fi not_active IP Right Cessation
- 1983-01-28 PH PH28446A patent/PH22625A/en unknown
- 1983-01-28 DE DE19833302814 patent/DE3302814A1/de active Granted
- 1983-01-31 NL NL8300350A patent/NL8300350A/nl not_active Application Discontinuation
- 1983-01-31 BE BE1/10709A patent/BE895751A/fr not_active IP Right Cessation
- 1983-01-31 FR FR8301586A patent/FR2520741B1/fr not_active Expired
- 1983-01-31 GB GB08302573A patent/GB2116171B/en not_active Expired
- 1983-02-01 CA CA000420692A patent/CA1193271A/en not_active Expired
- 1983-02-01 SE SE8300535A patent/SE455095B/sv not_active IP Right Cessation
- 1983-02-01 IL IL67813A patent/IL67813A0/xx not_active IP Right Cessation
- 1983-02-01 PT PT76175A patent/PT76175B/pt unknown
- 1983-02-01 AU AU10897/83A patent/AU569838B2/en not_active Ceased
- 1983-02-01 NZ NZ203144A patent/NZ203144A/en unknown
- 1983-02-01 DK DK040883A patent/DK160043C/da not_active IP Right Cessation
- 1983-02-02 HU HU83357A patent/HU190886B/hu not_active IP Right Cessation
- 1983-02-02 IE IE202/83A patent/IE55073B1/en not_active IP Right Cessation
- 1983-02-02 AT AT0034983A patent/AT391865B/de not_active IP Right Cessation
- 1983-02-02 ES ES519477A patent/ES519477A0/es active Granted
- 1983-02-02 JP JP58016866A patent/JPS58146580A/ja active Granted
- 1983-02-03 ZA ZA83733A patent/ZA83733B/xx unknown
- 1983-02-03 IT IT47666/83A patent/IT1197565B/it active
-
1986
- 1986-05-01 US US06/858,417 patent/US4737516A/en not_active Expired - Fee Related
-
1987
- 1987-12-30 MY MY167/87A patent/MY8700167A/xx unknown
-
1989
- 1989-03-27 SG SG162/89A patent/SG16289G/en unknown
- 1989-04-26 KE KE3877A patent/KE3877A/xx unknown
- 1989-06-15 HK HK477/89A patent/HK47789A/xx unknown
- 1989-12-08 CY CY1485A patent/CY1485A/en unknown
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