NO121546B - - Google Patents

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Info

Publication number: NO121546B
Authority: NO; Norway
Prior art keywords: compound; general formula; acid; formula; acid addition
Prior art date: 1967-04-21

Application number

NO1490/68A

Other languages

English (en)

Norwegian (no)

Inventor

J Earley

R Fryer

L Sternbach

Original Assignee

Hoffmann La Roche

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.)

1967-04-21

Filing date

1968-04-19

Publication date

1971-03-15

1968-04-19 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1971-03-15 Publication of NO121546B publication Critical patent/NO121546B/no

Links

150000001875 compounds Chemical class 0.000 claims description 22
150000003839 salts Chemical class 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 8
238000000034 method Methods 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
125000006239 protecting group Chemical group 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 3
125000003277 amino group Chemical group 0.000 claims description 3
229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 claims description 3
150000001557 benzodiazepines Chemical class 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
-1 ethylene, propylene Chemical group 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
229910052801 chlorine Inorganic materials 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
239000003158 myorelaxant agent Substances 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-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
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
229940125681 anticonvulsant agent Drugs 0.000 description 2
239000001961 anticonvulsive agent Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
238000007327 hydrogenolysis reaction Methods 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
239000000203 mixture Substances 0.000 description 2
229940035363 muscle relaxants Drugs 0.000 description 2
239000003921 oil Substances 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
229940125723 sedative agent Drugs 0.000 description 2
239000000932 sedative agent Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
239000012312 sodium hydride 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
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
ODWMYJHSPNKHNQ-UHFFFAOYSA-N C(C1=CC=CC=C1)OC(=O)NCCN1C(CN=C(C2=C1C=CC(=C2)Cl)C1=C(C=CC=C1)F)=O Chemical compound C(C1=CC=CC=C1)OC(=O)NCCN1C(CN=C(C2=C1C=CC(=C2)Cl)C1=C(C=CC=C1)F)=O ODWMYJHSPNKHNQ-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-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
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
125000004656 alkyl sulfonylamino group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
230000001773 anti-convulsant effect Effects 0.000 description 1
125000004657 aryl sulfonyl amino group Chemical group 0.000 description 1
MTDFNGLMQZRYJP-UHFFFAOYSA-N benzyl n-(2-chloroethyl)carbamate Chemical compound ClCCNC(=O)OCC1=CC=CC=C1 MTDFNGLMQZRYJP-UHFFFAOYSA-N 0.000 description 1
SDZIOSZETONVQE-UHFFFAOYSA-N benzyl n-(3-chloropropyl)carbamate Chemical compound ClCCCNC(=O)OCC1=CC=CC=C1 SDZIOSZETONVQE-UHFFFAOYSA-N 0.000 description 1
VYXYYVDRCHWCOP-UHFFFAOYSA-N benzyl n-(4-bromobutyl)carbamate Chemical compound BrCCCCNC(=O)OCC1=CC=CC=C1 VYXYYVDRCHWCOP-UHFFFAOYSA-N 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 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
125000004432 carbon atom Chemical group C* 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
UVCOILFBWYKHHB-UHFFFAOYSA-N desalkylflurazepam Chemical compound FC1=CC=CC=C1C1=NCC(=O)NC2=CC=C(Cl)C=C12 UVCOILFBWYKHHB-UHFFFAOYSA-N 0.000 description 1
MVAUDJDXZPBWOW-UHFFFAOYSA-N didesethylflurazepam Chemical compound N=1CC(=O)N(CCN)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1F MVAUDJDXZPBWOW-UHFFFAOYSA-N 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
229960003750 ethyl chloride Drugs 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
230000036571 hydration Effects 0.000 description 1
238000006703 hydration reaction Methods 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
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride 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
239000003326 hypnotic agent Substances 0.000 description 1
230000000147 hypnotic effect Effects 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000007788 liquid Substances 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
238000004519 manufacturing process Methods 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000012071 phase Substances 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
125000006248 tosyl amino group Chemical group [H]N(*)S(=O)(=O)C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- 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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material 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)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

NO1490/68A 1967-04-21 1968-04-19 NO121546B (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US63252967A	1967-04-21	1967-04-21
US67709267A	1967-10-23	1967-10-23

Publications (1)

Publication Number	Publication Date
NO121546B true NO121546B (de)	1971-03-15

Family

ID=27091656

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
NO1491/68A NO121665B (de)	1967-04-21	1968-04-19
NO1490/68A NO121546B (de)	1967-04-21	1968-04-19

Family Applications Before (1)

Application Number	Title	Priority Date	Filing Date
NO1491/68A NO121665B (de)	1967-04-21	1968-04-19

Country Status (16)

Country	Link
US (1)	US3464978A (de)
JP (1)	JPS5141640B1 (de)
AT (2)	AT278016B (de)
BE (2)	BE713828A (de)
CA (1)	CA948628A (de)
CH (4)	CH523895A (de)
DE (2)	DE1770206A1 (de)
ES (2)	ES352962A1 (de)
FI (1)	FI48090C (de)
FR (4)	FR1565036A (de)
GB (2)	GB1162949A (de)
IE (2)	IE32027B1 (de)
IL (2)	IL29772A (de)
NL (2)	NL6805555A (de)
NO (2)	NO121665B (de)
SE (3)	SE341405B (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS4837280B1 (de) *	1969-03-08	1973-11-09
US4251443A (en) *	1979-08-02	1981-02-17	Hoffmann-La Roche Inc.	Benzodiazepine derivatives
AT361492B (de) *	1978-12-18	1981-03-10	Gerot Pharmazeutika	Verfahren zur herstellung von neuen 3-hydroxy- 1,4-benzodiazepin-2-onen
CA1145333A (en) *	1980-02-08	1983-04-26	Quirico Branca	Benzodiazepine derivatives

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1051795A (de) *	1964-02-11

1967
- 1967-10-23 US US677092A patent/US3464978A/en not_active Expired - Lifetime
1968
- 1968-04-07 IL IL29772A patent/IL29772A/en unknown
- 1968-04-10 CH CH1787171A patent/CH523895A/de unknown
- 1968-04-10 CH CH1787271A patent/CH524561A/de not_active IP Right Cessation
- 1968-04-10 CH CH540968A patent/CH517752A/de not_active IP Right Cessation
- 1968-04-10 CH CH540868A patent/CH499525A/de not_active IP Right Cessation
- 1968-04-13 DE DE19681770206 patent/DE1770206A1/de active Pending
- 1968-04-13 DE DE19681770200 patent/DE1770200A1/de active Pending
- 1968-04-14 IL IL29818A patent/IL29818A/en unknown
- 1968-04-17 AT AT372968A patent/AT278016B/de not_active IP Right Cessation
- 1968-04-17 CA CA017,649A patent/CA948628A/en not_active Expired
- 1968-04-17 AT AT372868A patent/AT278015B/de not_active IP Right Cessation
- 1968-04-18 BE BE713828D patent/BE713828A/xx unknown
- 1968-04-18 BE BE713827D patent/BE713827A/xx unknown
- 1968-04-19 SE SE05323/68A patent/SE341405B/xx unknown
- 1968-04-19 NL NL6805555A patent/NL6805555A/xx unknown
- 1968-04-19 GB GB08511/68A patent/GB1162949A/en not_active Expired
- 1968-04-19 NL NL6805554A patent/NL6805554A/xx unknown
- 1968-04-19 GB GB08512/68A patent/GB1165112A/en not_active Expired
- 1968-04-19 NO NO1491/68A patent/NO121665B/no unknown
- 1968-04-19 FR FR1565036D patent/FR1565036A/fr not_active Expired
- 1968-04-19 SE SE5322/68A patent/SE343584B/xx unknown
- 1968-04-19 IE IE456/68A patent/IE32027B1/xx unknown
- 1968-04-19 NO NO1490/68A patent/NO121546B/no unknown
- 1968-04-19 IE IE455/68A patent/IE32026B1/xx unknown
- 1968-04-19 FR FR148694A patent/FR7602M/fr not_active Expired
- 1968-04-19 SE SE02511/71A patent/SE360080B/xx unknown
- 1968-04-20 JP JP43026179A patent/JPS5141640B1/ja active Pending
- 1968-04-20 ES ES352962A patent/ES352962A1/es not_active Expired
- 1968-04-20 ES ES352963A patent/ES352963A1/es not_active Expired
- 1968-04-22 FR FR148870A patent/FR7603M/fr not_active Expired
- 1968-04-22 FI FI681113A patent/FI48090C/fi active
- 1968-04-22 FR FR1565046D patent/FR1565046A/fr not_active Expired

Also Published As

Publication number	Publication date
SE360080B (de)	1973-09-17
SE343584B (de)	1972-03-13
US3464978A (en)	1969-09-02
IL29818A0 (en)	1968-06-20
CH524561A (de)	1972-06-30
FI48090C (fi)	1974-06-10
NO121665B (de)	1971-03-29
ES352963A1 (es)	1970-01-16
FR1565036A (de)	1969-04-25
NL6805555A (de)	1968-10-22
CH517752A (de)	1972-01-15
JPS5141640B1 (de)	1976-11-11
CH523895A (de)	1972-06-15
ES352962A1 (es)	1970-01-16
IE32026L (en)	1968-10-21
DE1770206A1 (de)	1971-09-23
IE32027B1 (en)	1973-03-21
FR7603M (de)	1970-01-19
IL29772A (en)	1971-11-29
IE32027L (en)	1968-10-21
IL29818A (en)	1971-12-29
FR7602M (de)	1970-01-19
SE341405B (de)	1971-12-27
AT278016B (de)	1970-01-26
AT278015B (de)	1970-01-26
DE1770200A1 (de)	1971-09-23
FI48090B (de)	1974-02-28
BE713828A (de)	1968-10-18
IL29772A0 (en)	1968-06-20
NL6805554A (de)	1968-10-22
GB1165112A (en)	1969-09-24
CA948628A (en)	1974-06-04
GB1162949A (en)	1969-09-04
BE713827A (de)	1968-10-18
FR1565046A (de)	1969-04-25
CH499525A (de)	1970-11-30
IE32026B1 (en)	1973-03-21

Publication	Publication Date	Title
AU646859B2 (en)	1994-03-10	4-(Piperazinyl, morpholinyl, or thiomorpholinyl) sulphonyl derivatives used as renin inhibitors, compositions and processes for their production
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