NO750263L - - Google Patents

Info

Publication number: NO750263L
Authority: NO; Norway
Prior art keywords: carbon atoms; alkoxy; hydroxy; alkyl; hydrogen
Prior art date: 1974-02-05

Application number

NO750263A

Other languages

English (en)

Norwegian (no)

Inventor

H Ott

R Sueess

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.)

1974-02-05

Filing date

1975-01-29

Publication date

1975-09-01

1975-01-29 Application filed by Sandoz Ag filed Critical Sandoz Ag

1975-09-01 Publication of NO750263L publication Critical patent/NO750263L/no

Links

125000004432 carbon atom Chemical group C* 0.000 claims description 69
125000003545 alkoxy group Chemical group 0.000 claims description 42
150000001875 compounds Chemical class 0.000 claims description 40
229910052739 hydrogen Inorganic materials 0.000 claims description 31
239000001257 hydrogen Substances 0.000 claims description 31
125000000217 alkyl group Chemical group 0.000 claims description 29
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 29
238000000034 method Methods 0.000 claims description 25
150000002431 hydrogen Chemical class 0.000 claims description 23
-1 benzyloxy, hydroxy Chemical group 0.000 claims description 20
238000006243 chemical reaction Methods 0.000 claims description 15
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 14
229910052736 halogen Inorganic materials 0.000 claims description 13
150000002367 halogens Chemical class 0.000 claims description 13
238000002360 preparation method Methods 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 11
125000001033 ether group Chemical group 0.000 claims description 10
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
239000000460 chlorine Substances 0.000 claims description 8
229910052801 chlorine Inorganic materials 0.000 claims description 8
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 8
BJVCSICIEDHBNI-UHFFFAOYSA-N benzo[b][1,8]naphthyridine Chemical group N1=CC=CC2=CC3=CC=CC=C3N=C21 BJVCSICIEDHBNI-UHFFFAOYSA-N 0.000 claims description 7
238000005661 deetherification reaction Methods 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 7
230000002829 reductive effect Effects 0.000 claims description 6
FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims description 3
SWJXWSAKHXBQSY-UHFFFAOYSA-N benzo(c)cinnoline Chemical group C1=CC=C2C3=CC=CC=C3N=NC2=C1 SWJXWSAKHXBQSY-UHFFFAOYSA-N 0.000 claims description 3
150000002391 heterocyclic compounds Chemical class 0.000 claims description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 44
230000008018 melting Effects 0.000 description 16
238000002844 melting Methods 0.000 description 16
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
238000006722 reduction reaction Methods 0.000 description 9
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
125000003277 amino group Chemical group 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
229910052763 palladium Inorganic materials 0.000 description 5
239000000047 product Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000000243 solution Substances 0.000 description 4
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-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
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000003776 cleavage reaction Methods 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
230000007017 scission Effects 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
239000007858 starting material Substances 0.000 description 3
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
208000009079 Bronchial Spasm Diseases 0.000 description 2
208000014181 Bronchial disease Diseases 0.000 description 2
206010006482 Bronchospasm Diseases 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
241000282326 Felis catus Species 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
239000003814 drug Substances 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
239000012458 free base Substances 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
229910052742 iron Inorganic materials 0.000 description 2
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
239000011976 maleic acid Substances 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
239000011707 mineral Substances 0.000 description 2
239000000203 mixture Substances 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
MUBZPKHOEPUJKR-UHFFFAOYSA-M oxalate(1-) Chemical compound OC(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-M 0.000 description 2
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
229910003446 platinum oxide Inorganic materials 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000007921 spray Substances 0.000 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 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
HPKWCZXGKDUJAA-UHFFFAOYSA-N 3-(4-methoxyphenyl)-1-methylpiperidin-4-amine Chemical compound C1=CC(OC)=CC=C1C1C(N)CCN(C)C1 HPKWCZXGKDUJAA-UHFFFAOYSA-N 0.000 description 1
KOVCKAZQEMBAAI-UHFFFAOYSA-N 3-(4-methoxyphenyl)-1-methylpiperidin-4-one Chemical compound C1=CC(OC)=CC=C1C1C(=O)CCN(C)C1 KOVCKAZQEMBAAI-UHFFFAOYSA-N 0.000 description 1
206010003598 Atelectasis Diseases 0.000 description 1
238000006407 Bischler-Napieralski reaction Methods 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
241000700198 Cavia Species 0.000 description 1
241000700199 Cavia porcellus Species 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
208000007123 Pulmonary Atelectasis Diseases 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
229910000564 Raney nickel Inorganic materials 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
238000003833 Wallach reaction Methods 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
229960004373 acetylcholine Drugs 0.000 description 1
125000004442 acylamino group Chemical group 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
208000006673 asthma Diseases 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 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
206010006451 bronchitis Diseases 0.000 description 1
230000001813 broncholytic effect Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000006114 decarboxylation reaction Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
MZQJXXGZGYLWMB-UHFFFAOYSA-N ethyl 3-amino-2-(4-methoxyphenyl)propanoate Chemical compound CCOC(=O)C(CN)C1=CC=C(OC)C=C1 MZQJXXGZGYLWMB-UHFFFAOYSA-N 0.000 description 1
MOMFMKUDFXSVIQ-UHFFFAOYSA-N ethyl 5-(4-methoxyphenyl)-1-methyl-4-oxopiperidine-3-carboxylate Chemical compound O=C1C(C(=O)OCC)CN(C)CC1C1=CC=C(OC)C=C1 MOMFMKUDFXSVIQ-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000006260 foam Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
229960001340 histamine Drugs 0.000 description 1
230000036571 hydration Effects 0.000 description 1
238000006703 hydration reaction Methods 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
229940071870 hydroiodic acid Drugs 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
TWOYTPGMVLCCQA-UHFFFAOYSA-N n-[3-(4-methoxyphenyl)-1-methylpiperidin-4-ylidene]hydroxylamine Chemical compound C1=CC(OC)=CC=C1C1C(=NO)CCN(C)C1 TWOYTPGMVLCCQA-UHFFFAOYSA-N 0.000 description 1
150000005054 naphthyridines Chemical class 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
230000000414 obstructive effect Effects 0.000 description 1
150000002923 oximes Chemical class 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
230000002980 postoperative effect Effects 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
238000006485 reductive methylation reaction Methods 0.000 description 1
208000023504 respiratory system disease Diseases 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
230000001148 spastic effect Effects 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NO750263A 1974-02-05 1975-01-29 NO750263L (da)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH155074		1974-02-05

Publications (1)

Publication Number	Publication Date
NO750263L true NO750263L (da)	1975-09-01

Family

ID=4213026

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO750263A NO750263L (da)	1974-02-05	1975-01-29

Country Status (19)

Country	Link
JP (1)	JPS50108297A (da)
AT (1)	AT351536B (da)
BE (1)	BE825124A (da)
CA (1)	CA1055944A (da)
DD (1)	DD117216A5 (da)
DE (1)	DE2503156A1 (da)
DK (1)	DK136189B (da)
ES (1)	ES434406A1 (da)
FI (1)	FI750205A (da)
FR (1)	FR2259611B1 (da)
GB (2)	GB1497722A (da)
HU (1)	HU169923B (da)
IL (1)	IL46553A (da)
NL (1)	NL7501159A (da)
NO (1)	NO750263L (da)
NZ (1)	NZ176550A (da)
PH (1)	PH11824A (da)
SE (1)	SE7500859L (da)
ZA (1)	ZA75743B (da)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8800397D0 (en) *	1988-01-08	1988-02-10	Sandoz Ltd	Improvements in/relating to organic compounds
MY105344A (en) *	1990-05-16	1994-09-30	Byk Gulden Lomberg Chemische Fabrik	New sulphonyl compounds

1975
- 1975-01-27 DK DK24275AA patent/DK136189B/da unknown
- 1975-01-27 SE SE7500859A patent/SE7500859L/xx unknown
- 1975-01-27 DE DE19752503156 patent/DE2503156A1/de active Pending
- 1975-01-27 FI FI750205A patent/FI750205A/fi not_active Application Discontinuation
- 1975-01-29 NO NO750263A patent/NO750263L/no unknown
- 1975-01-31 NL NL7501159A patent/NL7501159A/xx not_active Application Discontinuation
- 1975-02-03 ES ES434406A patent/ES434406A1/es not_active Expired
- 1975-02-03 PH PH16771A patent/PH11824A/en unknown
- 1975-02-03 DD DD183969A patent/DD117216A5/xx unknown
- 1975-02-03 NZ NZ176550A patent/NZ176550A/xx unknown
- 1975-02-03 IL IL46553A patent/IL46553A/en unknown
- 1975-02-03 HU HUSA2741A patent/HU169923B/hu unknown
- 1975-02-03 GB GB4516/75A patent/GB1497722A/en not_active Expired
- 1975-02-03 GB GB30857/77A patent/GB1497723A/en not_active Expired
- 1975-02-03 BE BE153007A patent/BE825124A/xx unknown
- 1975-02-04 JP JP50014021A patent/JPS50108297A/ja active Pending
- 1975-02-04 CA CA219,303A patent/CA1055944A/en not_active Expired
- 1975-02-04 AT AT79975A patent/AT351536B/de not_active IP Right Cessation
- 1975-02-05 FR FR7503547A patent/FR2259611B1/fr not_active Expired
- 1975-02-05 ZA ZA00750743A patent/ZA75743B/xx unknown

Also Published As

Publication number	Publication date
ZA75743B (en)	1976-09-29
GB1497723A (en)	1978-01-12
DK136189B (da)	1977-08-29
DK136189C (da)	1978-01-30
BE825124A (fr)	1975-08-04
ATA79975A (de)	1979-01-15
FI750205A (da)	1975-08-06
CA1055944A (en)	1979-06-05
AT351536B (de)	1979-07-25
PH11824A (en)	1978-07-19
FR2259611A1 (da)	1975-08-29
NZ176550A (en)	1978-09-25
DD117216A5 (da)	1976-01-05
GB1497722A (en)	1978-01-12
DE2503156A1 (de)	1975-08-07
ES434406A1 (es)	1977-03-01
JPS50108297A (da)	1975-08-26
DK24275A (da)	1975-09-29
SE7500859L (da)	1975-08-06
IL46553A0 (en)	1975-04-25
AU7784375A (en)	1976-08-05
IL46553A (en)	1977-12-30
HU169923B (da)	1977-02-28
FR2259611B1 (da)	1980-01-11
NL7501159A (nl)	1975-08-07

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US5324733A (en)	1994-06-28	Spirocyclic antipsychotic agents
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