NO127813B - - Google Patents

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Info

Publication number: NO127813B
Authority: NO; Norway
Prior art keywords: thieno; acid; dihydro; pyrrole; general formula
Prior art date: 1969-12-23

Application number

NO04844/70A

Other languages

English (en)

Norwegian (no)

Inventor

Hans Blattner

Walter Schindler

Original Assignee

Ciba Geigy Ag

Priority date (The priority date 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 date listed.)

1969-12-23

Filing date

1970-12-16

Publication date

1973-08-20

1970-12-16 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1973-08-20 Publication of NO127813B publication Critical patent/NO127813B/no

Links

150000001875 compounds Chemical class 0.000 claims description 39
150000003839 salts Chemical class 0.000 claims description 14
239000002253 acid Substances 0.000 claims description 10
238000000034 method Methods 0.000 claims description 10
150000007524 organic acids Chemical class 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
150000007522 mineralic acids Chemical class 0.000 claims description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
239000011593 sulfur Substances 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
150000003551 thiepines Chemical class 0.000 claims description 4
125000002252 acyl group Chemical group 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 3
235000005985 organic acids Nutrition 0.000 claims description 3
125000004432 carbon atom Chemical group C* 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
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 57
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 46
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 45
239000000243 solution Substances 0.000 description 40
-1 2- ethyl-2,3-dihydro-1H-thieno[2',3':2,3][1]benzothiepino[4,5-c]pyrrole Chemical compound 0.000 description 30
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 20
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
NIGNBCLEMMGDQP-UHFFFAOYSA-N 1-benzothiepine Chemical compound S1C=CC=CC2=CC=CC=C12 NIGNBCLEMMGDQP-UHFFFAOYSA-N 0.000 description 14
239000000203 mixture Substances 0.000 description 14
239000000126 substance Substances 0.000 description 14
238000001704 evaporation Methods 0.000 description 13
230000008020 evaporation Effects 0.000 description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 12
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 12
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 10
238000010992 reflux Methods 0.000 description 10
239000012043 crude product Substances 0.000 description 9
241001465754 Metazoa Species 0.000 description 8
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
229910000027 potassium carbonate Inorganic materials 0.000 description 8
229910052938 sodium sulfate Inorganic materials 0.000 description 8
235000011152 sodium sulphate Nutrition 0.000 description 8
239000002904 solvent Substances 0.000 description 8
238000003756 stirring Methods 0.000 description 8
239000000725 suspension Substances 0.000 description 8
239000012074 organic phase Substances 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
241000699670 Mus sp. Species 0.000 description 6
239000012442 inert solvent Substances 0.000 description 6
238000001953 recrystallisation Methods 0.000 description 6
238000012360 testing method Methods 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
231100000419 toxicity Toxicity 0.000 description 6
230000001988 toxicity Effects 0.000 description 6
239000002585 base Substances 0.000 description 5
239000007795 chemical reaction product Substances 0.000 description 5
PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 5
239000000155 melt Substances 0.000 description 5
229940098779 methanesulfonic acid Drugs 0.000 description 5
230000004899 motility Effects 0.000 description 5
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
235000019400 benzoyl peroxide Nutrition 0.000 description 4
238000009835 boiling Methods 0.000 description 4
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000011777 magnesium Substances 0.000 description 4
229910052749 magnesium Inorganic materials 0.000 description 4
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 4
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 4
NYJYBWMMIMNZIZ-UHFFFAOYSA-N 2H-[1]benzothiepino[4,5-c]pyrrole Chemical compound C1=C2C(=CN1)C=CSC1=C2C=CC=C1 NYJYBWMMIMNZIZ-UHFFFAOYSA-N 0.000 description 3
XJDDOXBKJTWRQN-UHFFFAOYSA-N 4,5-bis(bromomethyl)thieno[2,3-b][1]benzothiepine Chemical compound BrCC1=C(CBr)C2=CC=CC=C2SC2=C1C=CS2 XJDDOXBKJTWRQN-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
INCJCPHYKGMWLB-UHFFFAOYSA-N BrCC1=CC=CC(C=C2)=C1[S+](CBr)C1=C2SC=C1 Chemical compound BrCC1=CC=CC(C=C2)=C1[S+](CBr)C1=C2SC=C1 INCJCPHYKGMWLB-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
230000003444 anaesthetic effect Effects 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000003814 drug Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000012458 free base Substances 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
150000002431 hydrogen Chemical class 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
239000000047 product Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
150000003566 thiocarboxylic acids Chemical class 0.000 description 3
238000012345 traction test Methods 0.000 description 3
KMMMHDIESOWUFO-UHFFFAOYSA-N 13-thia-4-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),2(6),7,9,11,14,16-heptaene Chemical class C12=CC=CC=C2SC2=CC=CC=C2C2=C1CNC2 KMMMHDIESOWUFO-UHFFFAOYSA-N 0.000 description 2
KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 2
239000004342 Benzoyl peroxide Substances 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
UEPJPACCHTYPNY-UHFFFAOYSA-N C(C)OC(=O)N1CC2=C(C1)C1=C(SC3=C2C=CS3)C=CC=C1 Chemical compound C(C)OC(=O)N1CC2=C(C1)C1=C(SC3=C2C=CS3)C=CC=C1 UEPJPACCHTYPNY-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
150000001266 acyl halides Chemical class 0.000 description 2
230000029936 alkylation Effects 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
235000019270 ammonium chloride Nutrition 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
125000001589 carboacyl group Chemical group 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
125000004093 cyano group Chemical group *C#N 0.000 description 2
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000001640 fractional crystallisation Methods 0.000 description 2
239000005457 ice water Substances 0.000 description 2
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
230000003389 potentiating effect Effects 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
229960002317 succinimide Drugs 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
230000007306 turnover Effects 0.000 description 2
238000005303 weighing Methods 0.000 description 2
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
HJEOVBYPRBLZEG-UHFFFAOYSA-N 4,5-dimethylthieno[3,2-b][1]benzothiepine Chemical compound CC1=C(C)C2=CC=CC=C2SC2=C1SC=C2 HJEOVBYPRBLZEG-UHFFFAOYSA-N 0.000 description 1
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 1
ASUNAYOVHNVKFK-UHFFFAOYSA-N 5-methyl-5h-thieno[2,3-b][1]benzothiepin-4-one Chemical compound O=C1C(C)C2=CC=CC=C2SC2=C1C=CS2 ASUNAYOVHNVKFK-UHFFFAOYSA-N 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
POHZOAWOHVVUOE-UHFFFAOYSA-N C(CC)N1CC2=C(C1)C1=C(SC3=C2SC=C3)C=CC=C1 Chemical compound C(CC)N1CC2=C(C1)C1=C(SC3=C2SC=C3)C=CC=C1 POHZOAWOHVVUOE-UHFFFAOYSA-N 0.000 description 1
NHQMMNSYWQXOFN-UHFFFAOYSA-N C(CCC)N1CC2=C(C1)C1=C(SC3=C2SC=C3)C=CC=C1 Chemical compound C(CCC)N1CC2=C(C1)C1=C(SC3=C2SC=C3)C=CC=C1 NHQMMNSYWQXOFN-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
PAEYAKGINDQUCT-UHFFFAOYSA-N Ethyl 2-pyrrolecarboxylate Chemical compound CCOC(=O)C1=CC=CN1 PAEYAKGINDQUCT-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
231100000111 LD50 Toxicity 0.000 description 1
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229920005372 Plexiglas® Polymers 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-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
IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
AXNKGLDCLYLVLQ-UHFFFAOYSA-N acetamidoeugenol Chemical compound CCN(CC)C(=O)COC1=CC=C(CC=C)C=C1OC AXNKGLDCLYLVLQ-UHFFFAOYSA-N 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
FXXACINHVKSMDR-UHFFFAOYSA-N acetyl bromide Chemical compound CC(Br)=O FXXACINHVKSMDR-UHFFFAOYSA-N 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
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150000007513 acids Chemical class 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
230000002908 adrenolytic effect Effects 0.000 description 1
238000013019 agitation Methods 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001346 alkyl aryl ethers Chemical class 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
238000010171 animal model Methods 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
230000003042 antagnostic effect Effects 0.000 description 1
230000003474 anti-emetic effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000036760 body temperature Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
239000003874 central nervous system depressant Substances 0.000 description 1
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
230000001143 conditioned effect Effects 0.000 description 1
229940079593 drug Drugs 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
229960003750 ethyl chloride Drugs 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
210000004744 fore-foot Anatomy 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
229960001340 histamine Drugs 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
230000007794 irritation Effects 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 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
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
229960002510 mandelic acid Drugs 0.000 description 1
238000005259 measurement Methods 0.000 description 1
WREDNSAXDZCLCP-UHFFFAOYSA-N methanedithioic acid Chemical compound SC=S WREDNSAXDZCLCP-UHFFFAOYSA-N 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
239000011707 mineral Substances 0.000 description 1
229940035363 muscle relaxants Drugs 0.000 description 1
239000003158 myorelaxant agent Substances 0.000 description 1
230000003533 narcotic effect Effects 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
239000004926 polymethyl methacrylate Substances 0.000 description 1
230000011514 reflex Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
238000009864 tensile test Methods 0.000 description 1
231100001274 therapeutic index Toxicity 0.000 description 1
NRKMPGGGXCQLBG-UHFFFAOYSA-N thieno[2,3-b][1]benzothiepine Chemical compound C1=CC2=CC=CC=C2SC2=C1C=CS2 NRKMPGGGXCQLBG-UHFFFAOYSA-N 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- 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
- C07D495/12—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 three hetero rings
- C07D495/14—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NO04844/70A 1969-12-23 1970-12-16 NO127813B (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1906169A CH520699A (de)	1969-12-23	1969-12-23	Verfahren zur Herstellung von neuen Thiepinderivaten

Publications (1)

Publication Number	Publication Date
NO127813B true NO127813B (de)	1973-08-20

Family

ID=4437089

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO04844/70A NO127813B (de)	1969-12-23	1970-12-16

Country Status (4)

Country	Link
CH (3)	CH520699A (de)
GB (2)	GB1334540A (de)
NO (1)	NO127813B (de)
ZA (1)	ZA708615B (de)

1969
- 1969-12-23 CH CH1906169A patent/CH520699A/de not_active IP Right Cessation
- 1969-12-23 CH CH91372A patent/CH518961A/de not_active IP Right Cessation
- 1969-12-23 CH CH91472A patent/CH518962A/de not_active IP Right Cessation
1970
- 1970-12-16 NO NO04844/70A patent/NO127813B/no unknown
- 1970-12-17 GB GB1820573A patent/GB1334540A/en not_active Expired
- 1970-12-17 GB GB5983770A patent/GB1334539A/en not_active Expired
- 1970-12-22 ZA ZA708615A patent/ZA708615B/xx unknown

Also Published As

Publication number	Publication date
CH520699A (de)	1972-03-31
CH518961A (de)	1972-02-15
CH518962A (de)	1972-02-15
ZA708615B (en)	1971-10-27
GB1334540A (en)	1973-10-17
GB1334539A (en)	1973-10-17

Publication	Publication Date	Title
US3014911A (en)	1961-12-26	Derivatives of dibenzo[a, e]cycloheptatriene
NO156385B (no)	1987-06-01	Anordning for laasing av dreibare maskinelementer.
NO154554B (no)	1986-07-07	Fremgangsmaate til fremstilling av armeringsfibre for mineralske byggematerialer.
DE2125634A1 (de)	1972-01-05	Verfahren zur Herstellung von neuen Cycloheptenderivaten
NO142173B (no)	1980-03-31	Analogifremgangsmaate til fremstilling av terapeutisk virksomme, 1,1-diaryl-1-oksadiazolalkylaminderivater
DE69002079T2 (de)	1993-11-18	5,11-Dihydro-6H-dipyrido [3,2-b:2',3'-e]diazepin-6-one und deren Verwendung in der Vorbeugung und Behandlung von AIDS.
NO782108L (no)	1978-12-19	Nye hexahydropyrimidiner, fremgangsmaate til deres fremstilling og legemidler som inneholder disse forbindelser
SU603338A3 (ru)	1978-04-15	Способ получени производных тиенотиазина
US3636045A (en)	1972-01-18	Thiepino and oxepino(4 5-c)pyrrol derivatives
NO812529L (no)	1982-01-25	Analogifremgangsmaate for fremstilling av terapeutisk aktive dibenzo-diazepin-derivater
WO2023016249A1 (zh)	2023-02-16	3-芳氧基-3-五元杂芳基-丙胺类化合物的制备方法
NO750341L (de)	1975-09-01
NO151387B (no)	1984-12-17	Innstillingsinnretning for en elektronisk digitalindikator
IL29467A (en)	1973-01-30	N-phenyl indoline derivatives
NO127813B (de)	1973-08-20
KR100199299B1 (ko)	1999-06-15	벤조(c)페난트리디늄 유도체 제조방법 및 이 방법으로 제조된 신규화합물
NO122926B (de)	1971-09-06
NO124256B (de)	1972-03-27
NO121896B (de)	1971-04-26
DE69702955T2 (de)	2001-03-29	Bis-Imide Derivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zubereitung
CA1075688A (en)	1980-04-15	Iminodibenzyl derivatives
NO158736B (no)	1988-07-18	Analogifremgangsmaate for fremstilling av tetrahydropyridinderivater.
US4022780A (en)	1977-05-10	Process for the manufacture of indole derivatives
NO132355B (de)	1975-07-21
US3682959A (en)	1972-08-08	BENZOTHIEPINO{8 4,5-c{9 {0 PYRROLES