NO743036L - - Google Patents

Info

Publication number: NO743036L
Authority: NO; Norway
Prior art keywords: group; formula; hydrogen; compound; reacted
Prior art date: 1973-08-24

Application number

NO743036A

Other languages

English (en)

Norwegian (no)

Inventor

D H R Barton

R H Hesse

Original Assignee

Res Inst Medicine Chem

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.)

1973-08-24

Filing date

1974-08-23

Publication date

1975-03-24

1974-08-23 Application filed by Res Inst Medicine Chem filed Critical Res Inst Medicine Chem

1975-03-24 Publication of NO743036L publication Critical patent/NO743036L/no

Links

150000001875 compounds Chemical class 0.000 claims description 19
125000001424 substituent group Chemical group 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 10
238000004519 manufacturing process Methods 0.000 claims description 8
238000000034 method Methods 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 3
125000000623 heterocyclic group Chemical group 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
239000007858 starting material Substances 0.000 claims description 3
150000001408 amides Chemical class 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims 3
YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims 1
239000003638 chemical reducing agent Substances 0.000 claims 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
239000000243 solution Substances 0.000 description 16
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
229910052757 nitrogen Inorganic materials 0.000 description 7
-1 2-diethylamino- ethyl Chemical group 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
125000002252 acyl group Chemical group 0.000 description 5
125000005843 halogen group Chemical group 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
125000003545 alkoxy group Chemical group 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
230000001430 anti-depressive effect Effects 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 3
229960004801 imipramine Drugs 0.000 description 3
238000004452 microanalysis Methods 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
208000020401 Depressive disease Diseases 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
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 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
125000004414 alkyl thio group Chemical group 0.000 description 2
239000002168 alkylating agent Substances 0.000 description 2
229940100198 alkylating agent Drugs 0.000 description 2
239000000935 antidepressant agent Substances 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
230000008030 elimination Effects 0.000 description 2
238000003379 elimination reaction Methods 0.000 description 2
HJGNUWFEXJCWKN-UHFFFAOYSA-N ethyl n-[6-(2-phenylethenyl)cyclohexa-2,4-dien-1-ylidene]carbamate Chemical compound CCOC(=O)N=C1C=CC=CC1C=CC1=CC=CC=C1 HJGNUWFEXJCWKN-UHFFFAOYSA-N 0.000 description 2
239000000284 extract Substances 0.000 description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
235000012239 silicon dioxide Nutrition 0.000 description 2
239000011734 sodium Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
235000002906 tartaric acid Nutrition 0.000 description 2
239000011975 tartaric acid Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 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
SMBZJSVIKJMSFP-UHFFFAOYSA-N trifluoromethyl hypofluorite Chemical compound FOC(F)(F)F SMBZJSVIKJMSFP-UHFFFAOYSA-N 0.000 description 2
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical group OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
LCGTWRLJTMHIQZ-UHFFFAOYSA-N 5H-dibenzo[b,f]azepine Chemical compound C1=CC2=CC=CC=C2NC2=CC=CC=C21 LCGTWRLJTMHIQZ-UHFFFAOYSA-N 0.000 description 1
WXGBMVAPOXRLDB-UHFFFAOYSA-N 6-(2-phenylethenyl)cyclohexa-2,4-dien-1-imine Chemical class N=C1C=CC=CC1C=CC1=CC=CC=C1 WXGBMVAPOXRLDB-UHFFFAOYSA-N 0.000 description 1
238000006820 Bouveault-Blanc reduction reaction Methods 0.000 description 1
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-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
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 description 1
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-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
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000013543 active substance Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
125000004103 aminoalkyl group Chemical group 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 1
239000002585 base Substances 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
238000009835 boiling Methods 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
239000002775 capsule Substances 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000004663 dialkyl amino group Chemical group 0.000 description 1
125000004427 diamine group Chemical group 0.000 description 1
230000010339 dilation Effects 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
201000003104 endogenous depression Diseases 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000003682 fluorination reaction Methods 0.000 description 1
125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
238000001030 gas--liquid chromatography Methods 0.000 description 1
125000001188 haloalkyl group Chemical group 0.000 description 1
125000004997 halocarbonyl group Chemical group 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
208000024714 major depressive disease Diseases 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910001507 metal halide Inorganic materials 0.000 description 1
150000005309 metal halides Chemical class 0.000 description 1
229910000000 metal hydroxide Inorganic materials 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
GAYXVABTZIWOGW-UHFFFAOYSA-N n,n-dimethyl-3-[5-(trifluoromethoxy)benzo[b][1]benzazepin-11-yl]propan-1-amine Chemical compound C1=C(OC(F)(F)F)C2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 GAYXVABTZIWOGW-UHFFFAOYSA-N 0.000 description 1
HTJBEQIIIUXVIY-UHFFFAOYSA-N n-[6-(2-phenylethenyl)cyclohexa-2,4-dien-1-ylidene]acetamide Chemical compound CC(=O)N=C1C=CC=CC1C=CC1=CC=CC=C1 HTJBEQIIIUXVIY-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000000825 pharmaceutical preparation 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
150000003109 potassium Chemical class 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
150000003892 tartrate salts Chemical class 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
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
231100001274 therapeutic index Toxicity 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/18—Dibenzazepines; Hydrogenated dibenzazepines
- C07D223/22—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/18—Dibenzazepines; Hydrogenated dibenzazepines
- C07D223/22—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines
- C07D223/24—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines with hydrocarbon radicals, substituted by nitrogen atoms, attached to the ring nitrogen atom
- C07D223/26—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines with hydrocarbon radicals, substituted by nitrogen atoms, attached to the ring nitrogen atom having a double bond between positions 10 and 11

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)

NO743036A 1973-08-24 1974-08-23 NO743036L (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB4024273A GB1477635A (en)	1973-08-24	1973-08-24	Dibenzazepines

Publications (1)

Publication Number	Publication Date
NO743036L true NO743036L (fr)	1975-03-24

Family

ID=10413924

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO743036A NO743036L (fr)	1973-08-24	1974-08-23

Country Status (15)

Country	Link
JP (1)	JPS5070385A (fr)
AR (1)	AR206406A1 (fr)
BE (1)	BE819121A (fr)
CA (1)	CA1042887A (fr)
CH (1)	CH602658A5 (fr)
DE (1)	DE2440592A1 (fr)
DK (1)	DK450474A (fr)
FR (1)	FR2241319B1 (fr)
GB (1)	GB1477635A (fr)
IL (1)	IL45522A (fr)
NL (1)	NL7411235A (fr)
NO (1)	NO743036L (fr)
PH (1)	PH10437A (fr)
SE (1)	SE7410753L (fr)
ZA (1)	ZA745421B (fr)

1973
- 1973-08-24 GB GB4024273A patent/GB1477635A/en not_active Expired
1974
- 1974-01-01 AR AR255294A patent/AR206406A1/es active
- 1974-08-23 DE DE2440592A patent/DE2440592A1/de active Pending
- 1974-08-23 ZA ZA00745421A patent/ZA745421B/xx unknown
- 1974-08-23 DK DK450474A patent/DK450474A/da unknown
- 1974-08-23 BE BE147842A patent/BE819121A/fr unknown
- 1974-08-23 JP JP49096243A patent/JPS5070385A/ja active Pending
- 1974-08-23 NO NO743036A patent/NO743036L/no unknown
- 1974-08-23 FR FR7428988A patent/FR2241319B1/fr not_active Expired
- 1974-08-23 IL IL45522A patent/IL45522A/xx unknown
- 1974-08-23 SE SE7410753A patent/SE7410753L/xx unknown
- 1974-08-23 NL NL7411235A patent/NL7411235A/xx not_active Application Discontinuation
- 1974-08-23 PH PH16200A patent/PH10437A/en unknown
- 1974-08-23 CH CH1152774A patent/CH602658A5/xx not_active IP Right Cessation
- 1974-08-23 CA CA207,647A patent/CA1042887A/fr not_active Expired

Also Published As

Publication number	Publication date
PH10437A (en)	1977-03-21
CA1042887A (fr)	1978-11-21
CH602658A5 (fr)	1978-07-31
IL45522A (en)	1979-01-31
SE7410753L (fr)	1975-02-25
IL45522A0 (en)	1974-11-29
AR206406A1 (es)	1976-07-23
FR2241319A1 (fr)	1975-03-21
FR2241319B1 (fr)	1978-08-11
DK450474A (fr)	1975-04-28
DE2440592A1 (de)	1975-03-13
NL7411235A (nl)	1975-02-26
GB1477635A (en)	1977-06-22
JPS5070385A (fr)	1975-06-11
BE819121A (fr)	1975-02-24
ZA745421B (en)	1976-05-26

Publication	Publication Date	Title
KR20100018493A (ko)	2010-02-17	Ｄ3/ｄ2 길항제로서 신규한 피페라진 염
HU190984B (en)	1986-12-28	Process for producing new furo-, thieno- or pinolo-azepin derivatives
AU646485B2 (en)	1994-02-24	Indolonaphthyridines, their production and use
NO300806B1 (no)	1997-07-28	Substituerte (pyridinylamino)-benzisoksazoler og -benzo£b\|-tiofener, og deres anvendelse som medikamenter
NO172490B (no)	1993-04-19	Analogifremgangsmaate for fremstilling av terapeutisk aktive 1,4-disubstituerte piperazinderivater
IL95321A (en)	1994-02-27	4-Transformed History of G-) H] -014- Phnothiazine-01-Il (Alkyl [-2-Oxo-1-Oxa-8-Azaspiro] 4,5 [Decan, Preparation and Pharmaceutical Preparations Containing Them
WO2009065872A2 (fr)	2009-05-28	Procédés améliorés pour la synthèse de l-tartrate de varénicline
KR20060064682A (ko)	2006-06-13	4ａ,5,9,10,11,12-헥사하이드로벤조퓨로[3ａ,3,2][2]-벤자제핀의 신규한 유도체, 그의 제조방법 및 약물 제조에있어서의 그의 용도
IE46262B1 (en)	1983-04-20	Morphanthridines
NO743036L (fr)	1975-03-24
FI63014C (fi)	1983-04-11	Foer framstaellning av nya farmakologiskt aktiva aminobensocykloheptenderivat och deras salter avsedda 5-hydroxi- och 5-oxo-6,7,8,9-tetrahydroaminobensocykloheptenderivat och deras salter
Pawłowska et al.	2003	Stereoselective synthesis of (R)-(−)-mianserin
US4181655A (en)	1980-01-01	5(3-Substituted aminopropyl)-10-trifluoromethoxy-5H-dibenz[b,f]azepines
US4045443A (en)	1977-08-30	Organic compounds
GB1596170A (en)	1981-08-19	1,2,3,4,4a,10b-hexahydro-benz(f)isouqinolines
NZ205181A (en)	1986-07-11	2-methyl-lyserg-8-yl ethers and thioethers,a method for their preparation and pharmaceutical compositions which contain them
FI94759C (fi)	1995-10-25	Menetelmä terapeuttisesti käyttökelpoisten 1,2,3,3a,8,8a-heksahydro-1,3a,8-trimetyylipyrrolo/2,3b/indolijohdannaisten valmistamiseksi
AU2010362498B2 (en)	2016-04-28	Preparation process of (6R)-tetrahydrobiopterin hydrochloride
NO830877L (no)	1983-09-16	Tricykliske derivater av 5,6-dihydro-11h-dibenzo-(b,e)azepin-6-on med farmakologisk aktivitet og fremgangsmaate for deres fremstilling
JP2016513116A (ja)	2016-05-12	ジヒドロプテリジノンｉｉ
CA1140930A (fr)	1983-02-08	Amidines heterocycliques a liaison spirannique; leurs stereoisomeres et leurs isomeres optiques; methodes pour les preparer et medicaments contenant ces composes
Balaban et al.	2024	UNEXPECTED REARRANGEMENT OF PHENOXYPICRAMIDE TO 1, 3-DINITRO-10H-PHENOXAZINE
GB2024818A (en)	1980-01-16	Phenanthrene derivatives, their preparation and pharmaceutical compositions containing them
NZ223359A (en)	1991-03-26	(3s-cis)-3-ethyldihydro-4-((1-methyl-1h-diazol 5-yl)-methyl)-2(3h)-furanone derivatives and pharmaceutical compositions
US20100311734A1 (en)	2010-12-09	Spiro Compounds Useful as Antagonists of the H1 Receptor