DD158902A5 - Verfahren zur herstellung substituierter thienotricyclen - Google Patents
Verfahren zur herstellung substituierter thienotricyclen Download PDFInfo
- Publication number
- DD158902A5 DD158902A5 DD81229765A DD22976581A DD158902A5 DD 158902 A5 DD158902 A5 DD 158902A5 DD 81229765 A DD81229765 A DD 81229765A DD 22976581 A DD22976581 A DD 22976581A DD 158902 A5 DD158902 A5 DD 158902A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- group
- ethyl
- general formula
- substituted
- methyl
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- -1 morpholino, pyrrolidino, piperidino group Chemical group 0.000 claims abstract description 72
- 150000003839 salts Chemical class 0.000 claims abstract description 41
- 150000001875 compounds Chemical class 0.000 claims abstract description 35
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 35
- 238000000034 method Methods 0.000 claims abstract description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 20
- 238000002360 preparation method Methods 0.000 claims abstract description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 13
- 125000005843 halogen group Chemical group 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
- 239000002253 acid Substances 0.000 claims description 44
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 229910052801 chlorine Inorganic materials 0.000 claims description 17
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 17
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 125000002947 alkylene group Chemical group 0.000 claims description 11
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 8
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 8
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 8
- 239000002585 base Substances 0.000 claims description 7
- 230000010933 acylation Effects 0.000 claims description 6
- 238000005917 acylation reaction Methods 0.000 claims description 6
- 150000003335 secondary amines Chemical group 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 5
- 238000005576 amination reaction Methods 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 239000012458 free base Substances 0.000 claims description 4
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- UIOWABDOCRNXJM-UHFFFAOYSA-N 3-piperazin-1-yl-9h-thieno[2,3-i][1,2]benzodiazepine 8-oxide Chemical compound O=S1CC=C(C2=NN=3)C1=CC=C2C=CC=3N1CCNCC1 UIOWABDOCRNXJM-UHFFFAOYSA-N 0.000 claims description 2
- QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical group [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 claims 1
- 230000006203 ethylation Effects 0.000 claims 1
- 238000006200 ethylation reaction Methods 0.000 claims 1
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- 238000011282 treatment Methods 0.000 abstract description 4
- 210000000936 intestine Anatomy 0.000 abstract description 3
- 230000000144 pharmacologic effect Effects 0.000 abstract description 3
- 210000000056 organ Anatomy 0.000 abstract 2
- 210000002784 stomach Anatomy 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
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- 239000002904 solvent Substances 0.000 description 10
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- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 6
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 241000251730 Chondrichthyes Species 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
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- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000124008 Mammalia Species 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 239000000370 acceptor Substances 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
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- 150000004820 halides Chemical class 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- MJMZBXYBWMBFNY-UHFFFAOYSA-N methyl 4-(4-nitrophenoxy)butanoate Chemical compound COC(=O)CCCOC1=CC=C([N+]([O-])=O)C=C1 MJMZBXYBWMBFNY-UHFFFAOYSA-N 0.000 description 3
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- FMMUNDXXVADKHS-UHFFFAOYSA-N 1,3-dimethylpiperazine Chemical group CC1CN(C)CCN1 FMMUNDXXVADKHS-UHFFFAOYSA-N 0.000 description 2
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
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- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 229940049706 benzodiazepine Drugs 0.000 description 2
- 150000001557 benzodiazepines Chemical class 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
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- 125000004122 cyclic group Chemical group 0.000 description 2
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- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
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- PNVPNXKRAUBJGW-UHFFFAOYSA-N (2-chloroacetyl) 2-chloroacetate Chemical compound ClCC(=O)OC(=O)CCl PNVPNXKRAUBJGW-UHFFFAOYSA-N 0.000 description 1
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical class [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical class C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 description 1
- CPVWXPANROEFFD-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-thieno[2,3-i][1,2]benzodiazepine 8-oxide Chemical class N1NCCCC2=CC=C3S(=O)C=CC3=C21 CPVWXPANROEFFD-UHFFFAOYSA-N 0.000 description 1
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- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
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- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JTIGKVIOEQASGT-UHFFFAOYSA-N proquazone Chemical compound N=1C(=O)N(C(C)C)C2=CC(C)=CC=C2C=1C1=CC=CC=C1 JTIGKVIOEQASGT-UHFFFAOYSA-N 0.000 description 1
- 229960002466 proquazone Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- CYMJPJKHCSDSRG-UHFFFAOYSA-N pyrazolidine-3,4-dione Chemical class O=C1CNNC1=O CYMJPJKHCSDSRG-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006485 reductive methylation reaction Methods 0.000 description 1
- MOODSJOROWROTO-UHFFFAOYSA-N salicylsulfuric acid Chemical compound OC(=O)C1=CC=CC=C1OS(O)(=O)=O MOODSJOROWROTO-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
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- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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- 229940071103 sulfosalicylate Drugs 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940037128 systemic glucocorticoids Drugs 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000009492 tablet coating Methods 0.000 description 1
- 239000002700 tablet coating Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 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 description 1
- GKCBAIGFKIBETG-UHFFFAOYSA-N tetracaine Chemical compound CCCCNC1=CC=C(C(=O)OCCN(C)C)C=C1 GKCBAIGFKIBETG-UHFFFAOYSA-N 0.000 description 1
- 229960002372 tetracaine Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229960005344 tiapride Drugs 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 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
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Steroid Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH358180 | 1980-05-07 | ||
| CH65281 | 1981-02-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD158902A5 true DD158902A5 (de) | 1983-02-09 |
Family
ID=25685262
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD81229765A DD158902A5 (de) | 1980-05-07 | 1981-05-06 | Verfahren zur herstellung substituierter thienotricyclen |
Country Status (21)
| Country | Link |
|---|---|
| EP (1) | EP0039519B1 (pl) |
| JP (1) | JPS6021994B2 (pl) |
| KR (1) | KR850000241B1 (pl) |
| AT (1) | ATE7299T1 (pl) |
| AU (1) | AU538031B2 (pl) |
| DD (1) | DD158902A5 (pl) |
| DE (1) | DE3163361D1 (pl) |
| DK (1) | DK157872C (pl) |
| ES (1) | ES501929A0 (pl) |
| FI (1) | FI66002C (pl) |
| GR (1) | GR82676B (pl) |
| HK (1) | HK6890A (pl) |
| HU (1) | HU182712B (pl) |
| IE (1) | IE51200B1 (pl) |
| IL (1) | IL62792A (pl) |
| NO (1) | NO156753C (pl) |
| NZ (1) | NZ197017A (pl) |
| PL (1) | PL139428B1 (pl) |
| PT (1) | PT72982B (pl) |
| WO (1) | WO1981003173A1 (pl) |
| YU (1) | YU42398B (pl) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3204169A1 (de) * | 1982-02-06 | 1983-08-11 | Dr. Karl Thomae Gmbh, 7950 Biberach | Substituierte thienobenzodiazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE3204153A1 (de) * | 1982-02-06 | 1983-08-11 | Dr. Karl Thomae Gmbh, 7950 Biberach | Substituierte thienobenzodiazepinone, verfahren zu ihrer herstellung und sie enthaltende arzneimittel |
| DE3409237A1 (de) * | 1984-03-14 | 1985-09-19 | Dr. Karl Thomae Gmbh, 7950 Biberach | Kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE3529372A1 (de) * | 1985-08-16 | 1987-02-19 | Dompe Farmaceutici Spa | Aminoacyl-derivat von 4,9-dihydro-10h-pyrido(3,2-b)-thieno(3,2-e) (1,4)-diazepinon und von 4,9-dihydro-10h-pyrido(3,2-b)thieno(3,4-e) (1,4)diazepinon, verfahren zu deren herstellung und diese verbindungen enthaltende pharmazeutische zusammensetzungen |
| DE3643666A1 (de) * | 1986-12-20 | 1988-06-30 | Thomae Gmbh Dr K | Neue kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE3726908A1 (de) * | 1987-08-13 | 1989-02-23 | Thomae Gmbh Dr K | Neue kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| EP0386145A1 (de) * | 1987-12-22 | 1990-09-12 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Thienotricyclen zur behandlung von erkrankungen der bronchien |
| DE3802334A1 (de) * | 1988-01-27 | 1989-08-10 | Thomae Gmbh Dr K | Neue kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE3820346A1 (de) * | 1988-06-15 | 1989-12-21 | Thomae Gmbh Dr K | Neue kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE3820345A1 (de) * | 1988-06-15 | 1989-12-21 | Thomae Gmbh Dr K | Kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE4003322C1 (pl) * | 1990-02-05 | 1991-06-20 | Byk Gulden Lomberg Chemische Fabrik Gmbh, 7750 Konstanz, De |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1505795A (fr) * | 1965-12-17 | 1967-12-15 | Thomae Gmbh Dr K | Procédé pour fabriquer de nouvelles 11h-pyrido[2, 3-b][1, 5]benzodiazépine-5(6h)-ones substituées en position 11 |
| DE1795176C3 (de) * | 1968-08-20 | 1974-10-24 | Dr. Karl Thomae Gmbh, 7950 Biberach | hT-substituierte 5-Aminoacetyl-5,10-dihydro-l lH-dibenzo eckige Klammer auf b,e eckige Klammer zu eckige Klammer auf 1,4 eckige Klammer zu diazepin-11one und Verfahren zu ihrer Herstellung |
| DE1931487C3 (de) * | 1969-06-20 | 1975-12-18 | Dr. Karl Thomae Gmbh, 7950 Biberach | In 5-Stellung substituierte 5,10-Dihydro-11H-dibenzo eckige Klammer auf b,e eckige Klammer zu eckige Klammer auf 1,4 eckige Klammer zu diazepin-11 -one und Verfahren zu ihrer Herstellung |
| DE1795183B1 (de) * | 1968-08-20 | 1972-07-20 | Thomae Gmbh Dr K | 5,11-Dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-on-derivate und Arzneimittel |
| DE2424811C3 (de) * | 1974-05-22 | 1981-08-20 | Dr. Karl Thomae Gmbh, 7950 Biberach | Pyrido-benzodiazepinone, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel |
| SU629879A3 (ru) * | 1974-11-26 | 1978-10-25 | Лилли Индастриз Лимитед, (Фирма) | Способ получени тиено(1,5) бензодиазепинов или их солей |
| US4115568A (en) * | 1974-11-26 | 1978-09-19 | Lilly Industries Limited | Thieno[3,2-b]-[1,5]benzodiazepines |
| US4172831A (en) * | 1974-11-26 | 1979-10-30 | Lilly Industries Limited | Thieno-benzodiazepines |
| US3953430A (en) * | 1975-02-24 | 1976-04-27 | American Cyanamid Company | Substituted benzodiazepin-10-ones and method of use |
| US3951981A (en) * | 1975-02-24 | 1976-04-20 | American Cyanamid Company | Substituted benzodiazepines and method of use |
| US4144235A (en) * | 1978-03-13 | 1979-03-13 | American Cyanamid Company | Thieno[3,4-b][1,5]benzoxazepin-10-ones and thieno[3,4-b][1,5]benzothiazepin-10-ones |
| US4168269A (en) * | 1978-04-12 | 1979-09-18 | American Cyanamid Company | Substituted thieno-benzodiazepines |
| US4263207A (en) * | 1978-08-01 | 1981-04-21 | Merck & Co., Inc. | 10,11-Dihydrodibenzo[b,f][1,4]thiazepine carboxylic acids esters and amides thereof |
-
1981
- 1981-05-05 IL IL62792A patent/IL62792A/xx not_active IP Right Cessation
- 1981-05-06 EP EP81103437A patent/EP0039519B1/de not_active Expired
- 1981-05-06 GR GR64851A patent/GR82676B/el unknown
- 1981-05-06 AT AT81103437T patent/ATE7299T1/de not_active IP Right Cessation
- 1981-05-06 KR KR1019810001564A patent/KR850000241B1/ko not_active Expired
- 1981-05-06 PT PT72982A patent/PT72982B/pt unknown
- 1981-05-06 HU HU811799A patent/HU182712B/hu not_active IP Right Cessation
- 1981-05-06 WO PCT/EP1981/000042 patent/WO1981003173A1/de not_active Ceased
- 1981-05-06 NZ NZ197017A patent/NZ197017A/xx unknown
- 1981-05-06 DD DD81229765A patent/DD158902A5/de unknown
- 1981-05-06 ES ES501929A patent/ES501929A0/es active Granted
- 1981-05-06 AU AU70198/81A patent/AU538031B2/en not_active Ceased
- 1981-05-06 YU YU1161/81A patent/YU42398B/xx unknown
- 1981-05-06 JP JP56501690A patent/JPS6021994B2/ja not_active Expired
- 1981-05-06 IE IE997/81A patent/IE51200B1/en not_active IP Right Cessation
- 1981-05-06 PL PL1981231003A patent/PL139428B1/pl unknown
- 1981-05-06 DE DE8181103437T patent/DE3163361D1/de not_active Expired
- 1981-12-15 FI FI814028A patent/FI66002C/fi not_active IP Right Cessation
-
1982
- 1982-01-05 DK DK001582A patent/DK157872C/da not_active IP Right Cessation
- 1982-01-06 NO NO82820025A patent/NO156753C/no unknown
-
1990
- 1990-01-25 HK HK68/90A patent/HK6890A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO156753B (no) | 1987-08-10 |
| IE51200B1 (en) | 1986-10-29 |
| AU7019881A (en) | 1981-11-12 |
| PT72982A (en) | 1981-06-01 |
| ES8205802A1 (es) | 1982-08-16 |
| JPS6021994B2 (ja) | 1985-05-30 |
| IL62792A0 (en) | 1981-07-31 |
| KR830006300A (ko) | 1983-09-20 |
| EP0039519B1 (de) | 1984-05-02 |
| AU538031B2 (en) | 1984-07-26 |
| DK157872C (da) | 1990-07-30 |
| YU116181A (en) | 1984-02-29 |
| GR82676B (pl) | 1985-02-07 |
| HK6890A (en) | 1990-02-02 |
| PT72982B (fr) | 1982-10-21 |
| DK157872B (da) | 1990-02-26 |
| DK1582A (da) | 1982-01-05 |
| WO1981003173A1 (fr) | 1981-11-12 |
| FI66002C (fi) | 1984-08-10 |
| EP0039519A1 (de) | 1981-11-11 |
| PL231003A1 (pl) | 1981-12-23 |
| NO820025L (no) | 1982-01-06 |
| JPS57500695A (pl) | 1982-04-22 |
| FI66002B (fi) | 1984-04-30 |
| IE810997L (en) | 1981-11-07 |
| ES501929A0 (es) | 1982-08-16 |
| PL139428B1 (en) | 1987-01-31 |
| DE3163361D1 (en) | 1984-06-07 |
| HU182712B (en) | 1984-03-28 |
| NO156753C (no) | 1987-11-18 |
| ATE7299T1 (de) | 1984-05-15 |
| NZ197017A (en) | 1983-09-30 |
| KR850000241B1 (ko) | 1985-03-12 |
| IL62792A (en) | 1985-02-28 |
| YU42398B (en) | 1988-08-31 |
| FI814028L (fi) | 1981-12-15 |
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