CH416624A - Verfahren zur Herstellung von neuen heterocyclischen Verbindungen - Google Patents

Verfahren zur Herstellung von neuen heterocyclischen Verbindungen

Info

Publication number: CH416624A
Authority: CH; Switzerland
Prior art keywords: aza; methyl; chloro; formula; lower alkyl
Prior art date: 1962-10-23

Application number

CH1241162A

Other languages

German (de)

English (en)

Inventor

Ernst Dr Jucker

Anton Dr Ebnoether

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.)

1962-10-23

Filing date

1962-10-23

Publication date

1966-07-15

1962-10-23 Application filed by Sandoz Ag filed Critical Sandoz Ag

1962-10-23 Priority to CH1241162A priority Critical patent/CH416624A/de

1963-10-04 Priority to GB54512/65A priority patent/GB1058404A/en

1963-10-04 Priority to GB39118/63A priority patent/GB1058403A/en

1963-10-22 Priority to ES292760A priority patent/ES292760A2/es

1964-01-16 Priority to FR960559A priority patent/FR3323M/fr

1966-07-15 Publication of CH416624A publication Critical patent/CH416624A/de

Links

238000000034 method Methods 0.000 title claims description 11
238000002360 preparation method Methods 0.000 title claims description 5
150000002391 heterocyclic compounds Chemical class 0.000 title description 2
125000000217 alkyl group Chemical group 0.000 claims description 11
150000001875 compounds Chemical class 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
VEOSCXKPFWPNIA-UHFFFAOYSA-N thiochromeno[2,3-b]pyridin-5-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=N1 VEOSCXKPFWPNIA-UHFFFAOYSA-N 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 4
239000007795 chemical reaction product Substances 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
150000002901 organomagnesium compounds Chemical class 0.000 claims description 2
239000000047 product Substances 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
-1 aminopropyl halides Chemical class 0.000 description 10
239000000126 substance Substances 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
229960000583 acetic acid Drugs 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 7
239000000203 mixture Substances 0.000 description 7
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
229920000137 polyphosphoric acid Polymers 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
MYGXGCCFTPKWIH-UHFFFAOYSA-N 4-chloro-1-methylpiperidine Chemical compound CN1CCC(Cl)CC1 MYGXGCCFTPKWIH-UHFFFAOYSA-N 0.000 description 5
YMEPONLBONEIHQ-UHFFFAOYSA-N 7-chlorothiochromeno[2,3-b]pyridin-5-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=N1 YMEPONLBONEIHQ-UHFFFAOYSA-N 0.000 description 5
239000012362 glacial acetic acid Substances 0.000 description 5
230000007062 hydrolysis Effects 0.000 description 5
238000006460 hydrolysis reaction Methods 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
IBRSSZOHCGUTHI-UHFFFAOYSA-N 2-chloropyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=C1Cl IBRSSZOHCGUTHI-UHFFFAOYSA-N 0.000 description 4
FBRULNSXOMEFNA-UHFFFAOYSA-N 7-methylthiochromeno[2,3-b]pyridin-5-one Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3SC2=N1 FBRULNSXOMEFNA-UHFFFAOYSA-N 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
239000000155 melt Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
235000011121 sodium hydroxide Nutrition 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
GAAYPTPSHXSMEM-UHFFFAOYSA-N 5h-thiochromeno[2,3-b]pyridine Chemical class C1=CC=C2CC3=CC=CC=C3SC2=N1 GAAYPTPSHXSMEM-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
229940093915 gynecological organic acid Drugs 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
239000011777 magnesium Substances 0.000 description 3
229910052749 magnesium Inorganic materials 0.000 description 3
150000007522 mineralic acids Chemical class 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
150000007524 organic acids Chemical class 0.000 description 3
235000005985 organic acids Nutrition 0.000 description 3
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical group SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
YSBNBAYNISAUIT-UHFFFAOYSA-N 2-chloro-6-methylpyridine-3-carbonitrile Chemical compound CC1=CC=C(C#N)C(Cl)=N1 YSBNBAYNISAUIT-UHFFFAOYSA-N 0.000 description 2
NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 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
235000019270 ammonium chloride Nutrition 0.000 description 2
239000003814 drug Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
230000008030 elimination Effects 0.000 description 2
238000003379 elimination reaction Methods 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 2
239000001530 fumaric acid Substances 0.000 description 2
125000001188 haloalkyl group Chemical group 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
239000011630 iodine Substances 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
VRHHGFQAXXIRJW-UHFFFAOYSA-N 10h-thiochromeno[3,2-b]pyridine Chemical compound C1=CN=C2CC3=CC=CC=C3SC2=C1 VRHHGFQAXXIRJW-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
WVUULNDRFBHTFG-UHFFFAOYSA-N 3-chloro-n,n-diethylpropan-1-amine Chemical compound CCN(CC)CCCCl WVUULNDRFBHTFG-UHFFFAOYSA-N 0.000 description 1
RTEVQEDKZPFGNP-UHFFFAOYSA-N 4-bromo-1-methylpiperidine Chemical compound CN1CCC(Br)CC1 RTEVQEDKZPFGNP-UHFFFAOYSA-N 0.000 description 1
FTBCOQFMQSTCQQ-UHFFFAOYSA-N 4-bromobenzenethiol Chemical compound SC1=CC=C(Br)C=C1 FTBCOQFMQSTCQQ-UHFFFAOYSA-N 0.000 description 1
DTDXVJLMRMXSPU-UHFFFAOYSA-N 4-chloro-1-ethylpiperidine Chemical compound CCN1CCC(Cl)CC1 DTDXVJLMRMXSPU-UHFFFAOYSA-N 0.000 description 1
PAACGLGXFICDPG-UHFFFAOYSA-N 4-chloro-1-propan-2-ylpiperidine Chemical compound CC(C)N1CCC(Cl)CC1 PAACGLGXFICDPG-UHFFFAOYSA-N 0.000 description 1
VZXOZSQDJJNBRC-UHFFFAOYSA-N 4-chlorobenzenethiol Chemical compound SC1=CC=C(Cl)C=C1 VZXOZSQDJJNBRC-UHFFFAOYSA-N 0.000 description 1
WLHCBQAPPJAULW-UHFFFAOYSA-N 4-methylbenzenethiol Chemical compound CC1=CC=C(S)C=C1 WLHCBQAPPJAULW-UHFFFAOYSA-N 0.000 description 1
IWNPWQRBFNOGHM-UHFFFAOYSA-N 9h-thioxanthen-9-ol Chemical compound C1=CC=C2C(O)C3=CC=CC=C3SC2=C1 IWNPWQRBFNOGHM-UHFFFAOYSA-N 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
229910000861 Mg alloy Inorganic materials 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
208000010513 Stupor Diseases 0.000 description 1
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-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
OWXLRKWPEIAGAT-UHFFFAOYSA-N [Mg].[Cu] Chemical compound [Mg].[Cu] OWXLRKWPEIAGAT-UHFFFAOYSA-N 0.000 description 1
XACXNJHCZFUJON-UHFFFAOYSA-N [Na].ClC1=C(C=CC=C1)S Chemical compound [Na].ClC1=C(C=CC=C1)S XACXNJHCZFUJON-UHFFFAOYSA-N 0.000 description 1
150000007513 acids 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
230000008485 antagonism Effects 0.000 description 1
239000000935 antidepressant agent Substances 0.000 description 1
229940005513 antidepressants Drugs 0.000 description 1
229940125715 antihistaminic agent Drugs 0.000 description 1
239000000739 antihistaminic agent Substances 0.000 description 1
229940082988 antihypertensives serotonin antagonists Drugs 0.000 description 1
239000003420 antiserotonin agent Substances 0.000 description 1
239000006286 aqueous extract Substances 0.000 description 1
150000007514 bases Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 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
229940079593 drug Drugs 0.000 description 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
229960001340 histamine Drugs 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
239000005457 ice water Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 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
230000000701 neuroleptic effect Effects 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
KVNYFPKFSJIPBJ-UHFFFAOYSA-N ortho-diethylbenzene Natural products CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
229940076279 serotonin Drugs 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
238000010792 warming Methods 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

CH1241162A 1962-10-23 1962-10-23 Verfahren zur Herstellung von neuen heterocyclischen Verbindungen CH416624A (de)

Priority Applications (5)

Application Number	Priority Date	Filing Date	Title
CH1241162A CH416624A (de)	1962-10-23	1962-10-23	Verfahren zur Herstellung von neuen heterocyclischen Verbindungen
GB54512/65A GB1058404A (en)	1962-10-23	1963-10-04	4-azathiaxanthone derivatives
GB39118/63A GB1058403A (en)	1962-10-23	1963-10-04	Improvements in or relating to novel 4-aza-thiaxanthene derivatives
ES292760A ES292760A2 (es)	1962-10-23	1963-10-22	Procedimiento de obtención de derivados de 4-aza-tia-xanteno
FR960559A FR3323M (fr)	1962-10-23	1964-01-16	Médicament a base de dérivé de l'aza-thiaxanthene.

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1241162A CH416624A (de)	1962-10-23	1962-10-23	Verfahren zur Herstellung von neuen heterocyclischen Verbindungen

Publications (1)

Publication Number	Publication Date
CH416624A true CH416624A (de)	1966-07-15

Family

ID=4382748

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1241162A CH416624A (de)	1962-10-23	1962-10-23	Verfahren zur Herstellung von neuen heterocyclischen Verbindungen

Country Status (4)

Country	Link
CH (1)	CH416624A (fr)
ES (1)	ES292760A2 (fr)
FR (1)	FR3323M (fr)
GB (2)	GB1058404A (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7541365B2 (en)	2001-11-21	2009-06-02	Millennium Pharmaceuticals, Inc.	Chemokine receptor antagonists and methods of use therefor
TWI291467B (en)	2002-11-13	2007-12-21	Millennium Pharm Inc	CCR1 antagonists and methods of use therefor

1962
- 1962-10-23 CH CH1241162A patent/CH416624A/de unknown
1963
- 1963-10-04 GB GB54512/65A patent/GB1058404A/en not_active Expired
- 1963-10-04 GB GB39118/63A patent/GB1058403A/en not_active Expired
- 1963-10-22 ES ES292760A patent/ES292760A2/es not_active Expired
1964
- 1964-01-16 FR FR960559A patent/FR3323M/fr not_active Expired

Also Published As

Publication number	Publication date
GB1058403A (en)	1967-02-08
FR3323M (fr)	1965-05-17
GB1058404A (en)	1967-02-08
ES292760A2 (es)	1964-04-16

Publication	Publication Date	Title
DE2111071A1 (de)	1971-09-23	Verfahren zur Herstellung neuer heterocyclischer Verbindungen
AT200578B (de)	1958-11-10	Verfahren zur Herstellung von neuen N-Aminoalkylderivaten von Azepinen
CH416624A (de)	1966-07-15	Verfahren zur Herstellung von neuen heterocyclischen Verbindungen
DE1206437B (de)	1965-12-09	Verfahren zur Herstellung von neuen 4-Aza-thioxanthenderivaten
CH638525A5 (de)	1983-09-30	3-(tetrazol-5-yl)-1-azaxanthone und verfahren zu ihrer herstellung.
DE1620437A1 (de)	1970-03-12	Neue heterocyclische Verbindungen sowie Verfahren zu ihrer Herstellung
AT230388B (de)	1963-12-10	Verfahren zur Herstellung von neuen 4-Aza-thioxanthen-Derivaten
AT328445B (de)	1976-03-25	Verfahren zur herstellung neuer 4- (1-alkyl-4-piperidyliden) -4h-benzo (4,5) cyclohepta (1,2-b)thiophen-10 (9h) -on verbindungen und ihrer saureadditionssalze
AT230373B (de)	1963-12-10	Verfahren zur Herstellung von neuen Dibenzocycloheptan-Derivaten
AT233552B (de)	1964-05-11	Verfahren zur Herstellung von neuen Dibenzocycloheptadien-Derivaten und ihren Salzen
CH387638A (de)	1965-02-15	Verfahren zur Herstellung von neuen heterocyclischen Verbindungen
AT226724B (de)	1963-04-10	Verfahren zur Herstellung von neuen 1-Aza-thioxanthen-Derivaten
AT211821B (de)	1960-11-10	Verfahren zur Herstellung Alkylaminoacetaryliden
DE1246741B (de)	1967-08-10	Verfahren zur Herstellung von neuen ungesaettigten Dibenzocycloheptan-Derivaten
DE2614836A1 (de)	1976-10-21	Neue chromonverbindungen, verfahren zu ihrer herstellung und sie enthaltende arzneimittelzubereitungen
AT371448B (de)	1983-06-27	Verfahren zur herstellung von neuen cis-4a-phenyl -isochinolin-derivaten und ihren saeureadditionssalzen
CH405354A (de)	1966-01-15	Verfahren zur Herstellung von neuen heterocyclischen Verbindungen
AT230389B (de)	1963-12-10	Verfahren zur Herstellung von neuen Thioxanthen-Derivaten
AT226235B (de)	1963-03-11	Verfahren zur Herstellung von neuen Thioxanthen-Derivaten
CH537404A (de)	1973-05-31	Verfahren zur Herstellung neuer Thiophenderivate
AT228217B (de)	1963-07-10	Verfahren zur Herstellung von neuen Homothioxanthen-Derivaten
AT234679B (de)	1964-07-10	Verfahren zur Herstellung von neuen Amino-pyrazol-Derivaten
AT262271B (de)	1968-06-10	Verfahren zur Herstellung neuer 9,10-Dihydro-4H-benzo[4,5]cyclohepta[1,2-b]thiophen-Derivate und ihrer Salze
AT222127B (de)	1962-07-10	Verfahren zur Herstellung von neuen Thioxanthen-Derivaten
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