CH472404A - Verfahren zur Herstellung neuer Indolderivate - Google Patents

Verfahren zur Herstellung neuer Indolderivate

Info

Publication number: CH472404A
Authority: CH; Switzerland
Prior art keywords: formula; reaction; acid; methyl; epichlorohydrin
Prior art date: 1966-03-04

Application number

CH315466A

Other languages

German (de)

English (en)

Inventor

Franz Dr Troxler

Original Assignee

Sandoz 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.)

1966-03-04

Filing date

1966-03-04

Publication date

1969-05-15

1966-03-04 Application filed by Sandoz Ag filed Critical Sandoz Ag

1966-03-04 Priority to CH315466A priority Critical patent/CH472404A/de

1967-03-02 Priority to FI61667A priority patent/FI47365C/fi

1967-03-02 Priority to CS155667A priority patent/CS156406B2/cs

1967-03-02 Priority to ES337457A priority patent/ES337457A1/es

1967-03-03 Priority to DK112867A priority patent/DK121168B/da

1967-03-03 Priority to SE293067A priority patent/SE308720B/xx

1967-03-03 Priority to AT205967A priority patent/AT266112B/de

1969-05-15 Publication of CH472404A publication Critical patent/CH472404A/de

Links

238000000034 method Methods 0.000 title claims description 12
229940054051 antipsychotic indole derivative Drugs 0.000 title claims description 3
150000002475 indoles Chemical class 0.000 title claims description 3
238000004519 manufacturing process Methods 0.000 title description 2
238000006243 chemical reaction Methods 0.000 claims description 9
150000001875 compounds Chemical class 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
NLMQHXUGJIAKTH-UHFFFAOYSA-N 4-hydroxyindole Chemical class OC1=CC=CC2=C1C=CN2 NLMQHXUGJIAKTH-UHFFFAOYSA-N 0.000 claims description 6
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
150000001412 amines Chemical class 0.000 claims description 5
239000007795 chemical reaction product Substances 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
230000007717 exclusion Effects 0.000 claims description 3
150000007522 mineralic acids Chemical class 0.000 claims description 3
150000007524 organic acids Chemical class 0.000 claims description 3
235000005985 organic acids Nutrition 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
239000011230 binding agent Substances 0.000 claims description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000000243 solution Substances 0.000 description 5
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
239000000203 mixture Substances 0.000 description 4
229910052763 palladium Inorganic materials 0.000 description 4
-1 potassium carbonate Chemical class 0.000 description 4
JHFAEUICJHBVHB-UHFFFAOYSA-N 1h-indol-2-ol Chemical compound C1=CC=C2NC(O)=CC2=C1 JHFAEUICJHBVHB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
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 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
235000002906 tartaric acid Nutrition 0.000 description 3
238000011282 treatment Methods 0.000 description 3
LJFVSIDBFJPKLD-UHFFFAOYSA-N 4-phenylmethoxy-1h-indole Chemical compound C=1C=CC=2NC=CC=2C=1OCC1=CC=CC=C1 LJFVSIDBFJPKLD-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-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
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
208000001871 Tachycardia Diseases 0.000 description 2
UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
239000012670 alkaline solution Substances 0.000 description 2
206010003119 arrhythmia Diseases 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
229940093915 gynecological organic acid Drugs 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
NXWGWUVGUSFQJC-UHFFFAOYSA-N mepindolol Chemical compound CC(C)NCC(O)COC1=CC=CC2=C1C=C(C)N2 NXWGWUVGUSFQJC-UHFFFAOYSA-N 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
230000006794 tachycardia Effects 0.000 description 2
239000011975 tartaric acid Substances 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
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
FGGWBXKCGYCYGV-UHFFFAOYSA-N 1-(1-methylindol-4-yl)oxy-3-(propan-2-ylamino)propan-2-ol Chemical compound C(C)(C)NCC(COC1=C2C=CN(C2=CC=C1)C)O FGGWBXKCGYCYGV-UHFFFAOYSA-N 0.000 description 1
YIUIPTVCXWPNJM-UHFFFAOYSA-N 1-(butan-2-ylamino)-3-(1H-indol-4-yloxy)propan-2-ol Chemical compound CCC(C)NCC(COC1=CC=CC2=C1C=CN2)O YIUIPTVCXWPNJM-UHFFFAOYSA-N 0.000 description 1
AADKPSZXBUUSOX-UHFFFAOYSA-N 1-(cyclopropylamino)-3-(1H-indol-4-yloxy)propan-2-ol Chemical compound OC(COC1=C2C=CNC2=CC=C1)CNC1CC1 AADKPSZXBUUSOX-UHFFFAOYSA-N 0.000 description 1
QMHJCIVEEBUCFP-UHFFFAOYSA-N 1-[(3-methyl-1h-indol-4-yl)oxy]-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(O)COC1=CC=CC2=C1C(C)=CN2 QMHJCIVEEBUCFP-UHFFFAOYSA-N 0.000 description 1
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
PXYRYFLSOOBYGT-UHFFFAOYSA-N 2-(4-phenylmethoxy-1H-indol-2-yl)acetonitrile Chemical compound C(C1=CC=CC=C1)OC1=C2C=C(NC2=CC=C1)CC#N PXYRYFLSOOBYGT-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
BGQHPLYSXBZMQG-UHFFFAOYSA-N 4-(2-Hydroxy-3-tert-butylaminopropoxy)-2-methylindole Chemical compound C1=CC=C2NC(C)=CC2=C1OCC(O)CNC(C)(C)C BGQHPLYSXBZMQG-UHFFFAOYSA-N 0.000 description 1
BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
WUCPCORZZJWVHG-UHFFFAOYSA-N 4-bromo-2-propylthiophene Chemical compound CCCC1=CC(Br)=CS1 WUCPCORZZJWVHG-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 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
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
XADCESSVHJOZHK-UHFFFAOYSA-N Meperidine Chemical class C=1C=CC=CC=1C1(C(=O)OCC)CCN(C)CC1 XADCESSVHJOZHK-UHFFFAOYSA-N 0.000 description 1
240000007817 Olea europaea Species 0.000 description 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
230000000323 adipokinetic effect Effects 0.000 description 1
230000001800 adrenalinergic effect Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
230000003276 anti-hypertensive effect Effects 0.000 description 1
230000006793 arrhythmia Effects 0.000 description 1
239000002585 base Substances 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
208000006218 bradycardia Diseases 0.000 description 1
230000036471 bradycardia Effects 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
150000001720 carbohydrates Chemical class 0.000 description 1
235000014633 carbohydrates Nutrition 0.000 description 1
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
239000003086 colorant Substances 0.000 description 1
208000029078 coronary artery disease Diseases 0.000 description 1
238000012937 correction Methods 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
IZEKFCXSFNUWAM-UHFFFAOYSA-N dipyridamole Chemical compound C=12N=C(N(CCO)CCO)N=C(N3CCCCC3)C2=NC(N(CCO)CCO)=NC=1N1CCCCC1 IZEKFCXSFNUWAM-UHFFFAOYSA-N 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000001834 epinephrinelike Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 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
238000007327 hydrogenolysis reaction Methods 0.000 description 1
125000001041 indolyl group Chemical group 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
229960001317 isoprenaline Drugs 0.000 description 1
LYBKPDDZTNUNNM-UHFFFAOYSA-N isopropylbenzylamine Chemical compound CC(C)NCC1=CC=CC=C1 LYBKPDDZTNUNNM-UHFFFAOYSA-N 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate 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
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
210000000653 nervous system Anatomy 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
150000007530 organic bases Chemical group 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
JZQKKSLKJUAGIC-UHFFFAOYSA-N pindolol Chemical compound CC(C)NCC(O)COC1=CC=CC2=C1C=CN2 JZQKKSLKJUAGIC-UHFFFAOYSA-N 0.000 description 1
229940072033 potash Drugs 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Indole Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH315466A 1966-03-04 1966-03-04 Verfahren zur Herstellung neuer Indolderivate CH472404A (de)

Priority Applications (7)

Application Number	Priority Date	Filing Date	Title
CH315466A CH472404A (de)	1966-03-04	1966-03-04	Verfahren zur Herstellung neuer Indolderivate
FI61667A FI47365C (fi)	1966-03-04	1967-03-02	Menetelmä valmistaa uusia terapeuttisesti vaikuttavia indolijohdannais ia.
CS155667A CS156406B2 (cs)	1966-03-04	1967-03-02
ES337457A ES337457A1 (es)	1966-03-04	1967-03-02	Procedimiento para la produccion de derivados indolicos.
DK112867A DK121168B (da)	1966-03-04	1967-03-03	Fremgangsmåde til fremstilling af indolderivater.
SE293067A SE308720B (cs)	1966-03-04	1967-03-03
AT205967A AT266112B (de)	1966-03-04	1967-03-03	Verfahren zur Herstellung neuer Indolderivate und ihrer Salze

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH315466A CH472404A (de)	1966-03-04	1966-03-04	Verfahren zur Herstellung neuer Indolderivate

Publications (1)

Publication Number	Publication Date
CH472404A true CH472404A (de)	1969-05-15

Family

ID=4249777

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH315466A CH472404A (de)	1966-03-04	1966-03-04	Verfahren zur Herstellung neuer Indolderivate

Country Status (7)

Country	Link
AT (1)	AT266112B (cs)
CH (1)	CH472404A (cs)
CS (1)	CS156406B2 (cs)
DK (1)	DK121168B (cs)
ES (1)	ES337457A1 (cs)
FI (1)	FI47365C (cs)
SE (1)	SE308720B (cs)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2004017964A1 (en)	2002-08-19	2004-03-04	Pfizer Products Inc.	Combination therapy for hyperproliferative diseases
WO2007024945A1 (en)	2005-08-25	2007-03-01	Novartis Ag	Condensed imidazolo derivatives for the inhibition of aldosterone synthase and aromatase
WO2007062314A2 (en)	2005-11-23	2007-05-31	Bristol-Myers Squibb Company	Heterocyclic cetp inhibitors
WO2008070496A2 (en)	2006-12-01	2008-06-12	Bristol-Myers Squibb Company	N- ( (3-benzyl) -2, 2- (bis-phenyl) -propan-1-amine derivatives as cetp inhibitors for the treatment of atherosclerosis and cardiovascular diseases
EP2392567A1 (en)	2005-10-21	2011-12-07	Bristol-Myers Squibb Company	Benzothiazine derivatives and their use as lxr modulators
WO2014170786A1 (en)	2013-04-17	2014-10-23	Pfizer Inc.	N-piperidin-3-ylbenzamide derivatives for treating cardiovascular diseases
WO2016055901A1 (en)	2014-10-08	2016-04-14	Pfizer Inc.	Substituted amide compounds
US10251959B2 (en)	2007-03-12	2019-04-09	Nektar Therapeutics	Oligomer-beta blocker conjugates
WO2020150473A2 (en)	2019-01-18	2020-07-23	Dogma Therapeutics, Inc.	Pcsk9 inhibitors and methods of use thereof

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
MC1357A1 (fr) *	1979-12-07	1981-08-10	Hoffmann La Roche	Derives de 2,3-indoledione

1966
- 1966-03-04 CH CH315466A patent/CH472404A/de not_active IP Right Cessation
1967
- 1967-03-02 ES ES337457A patent/ES337457A1/es not_active Expired
- 1967-03-02 CS CS155667A patent/CS156406B2/cs unknown
- 1967-03-02 FI FI61667A patent/FI47365C/fi active
- 1967-03-03 SE SE293067A patent/SE308720B/xx unknown
- 1967-03-03 AT AT205967A patent/AT266112B/de active
- 1967-03-03 DK DK112867A patent/DK121168B/da unknown

Cited By (13)

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Also Published As

Publication number	Publication date
ES337457A1 (es)	1968-03-01
DK121168B (da)	1971-09-20
AT266112B (de)	1968-11-11
SE308720B (cs)	1969-02-24
FI47365C (fi)	1973-11-12
FI47365B (cs)	1973-07-31
CS156406B2 (cs)	1974-07-24

Legal Events

Date	Code	Title	Description
1986-05-30	PL	Patent ceased

Publication	Publication Date	Title
DE1963182A1 (de)	1970-10-15	Neue N-Phenylindolin-Derivate und deren Verwendung als Arzneimittel
CH472404A (de)	1969-05-15	Verfahren zur Herstellung neuer Indolderivate
CH301670A (de)	1954-09-15	Verfahren zur Herstellung eines Morphinanabkömmlings.
DE934651C (de)	1955-11-03	Verfahren zur Herstellung von tetrasubstituierten Diaminoalkanen
DE2639291C2 (cs)	1987-05-27
DE1905881A1 (de)	1969-09-25	Verfahren zur Herstellung neuer heterocyclischer Verbindungen
CH523884A (de)	1972-06-15	Verfahren zur Herstellung neuer Indol-Derivate
AT303025B (de)	1972-10-15	Verfahren zur herstellung neuer indolderivate und ihrer saeureadditionssalze
DE1620342C3 (cs)	1974-05-16
CH535236A (de)	1973-03-31	Verfahren zur Herstellung neuer reaktionsträger Lysergsäurederivate
DE745314C (de)	1944-11-27	Verfahren zur Herstellung von analgetisch wirkenden 1-Oxyphenyl-3-aminoalkylverbindungen
AT250338B (de)	1966-11-10	Verfahren zur Herstellung neuer, basischer Derivate von substituierten Benzofuran-2-carbonsäuren und deren Salzen
CH473821A (de)	1969-06-15	Verfahren zur Herstellung von Iminodibenzyl-Derivaten
CH511839A (de)	1971-08-31	Verfahren zur Herstellung neuer Indolverbindungen
AT235283B (de)	1964-08-25	Verfahren zur Herstellung neuer Indolverbindungen
AT255422B (de)	1967-07-10	Verfahren zur Herstellung von neuen Iminodibenzylderivaten
AT213885B (de)	1961-03-10	Verfahren zur Herstellung von neuen Indol-Derivaten
CH483423A (de)	1969-12-31	Verfahren zur Herstellung einer neuen Indolverbindung
CH543505A (de)	1973-10-31	Verfahren zur Herstellung neuer Indolderivate
DE2345651A1 (de)	1974-03-28	Indolylalkylamine und verfahren zu ihrer herstellung
AT360992B (de)	1981-02-10	Verfahren zur herstellung neuer phenylazacyclo- alkane und von deren salzen und optisch aktiven verbindungen
AT400146B (de)	1995-10-25	Verfahren zur herstellung von 1-(2-((5-
CH636101A5 (en)	1983-05-13	Process for preparing novel condensed derivatives of pyrimidine
CH502337A (de)	1971-01-31	Verfahren zur Herstellung neuer Indolderivate
CH526541A (de)	1972-08-15	Verfahren zur Herstellung neuer Indolderivate