NO781333L - Fremgangsmaate til fremstilling av 2-(2,2-diarylalkyl)-1-azabicyklo(2.2.2)ocetan og beslektede forbindelser - Google Patents

Fremgangsmaate til fremstilling av 2-(2,2-diarylalkyl)-1-azabicyklo(2.2.2)ocetan og beslektede forbindelser

Info

Publication number: NO781333L
Authority: NO; Norway
Prior art keywords: azabicyclo; octane; diphenylethyl; pharmaceutically acceptable; acid addition
Prior art date: 1977-04-18

Application number

NO781333A

Other languages

English (en)

Norwegian (no)

Inventor

Chung Hwai Yen

Original Assignee

Searle & Co

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.)

1977-04-18

Filing date

1978-04-17

Publication date

1978-10-19

1978-04-17 Application filed by Searle & Co filed Critical Searle & Co

1978-10-19 Publication of NO781333L publication Critical patent/NO781333L/no

Links

150000001875 compounds Chemical class 0.000 title claims description 51
238000000034 method Methods 0.000 title claims description 32
238000002360 preparation method Methods 0.000 title claims description 6
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 44
-1 alkyl radical Chemical class 0.000 claims description 27
125000004432 carbon atom Chemical group C* 0.000 claims description 25
KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims description 21
239000002253 acid Substances 0.000 claims description 19
150000003839 salts Chemical class 0.000 claims description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 claims description 4
125000005037 alkyl phenyl group Chemical group 0.000 claims description 4
125000005059 halophenyl group Chemical group 0.000 claims description 4
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
BRTFVKHPEHKBQF-UHFFFAOYSA-N bromocyclopentane Chemical compound BrC1CCCC1 BRTFVKHPEHKBQF-UHFFFAOYSA-N 0.000 claims description 3
KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
125000004076 pyridyl group Chemical group 0.000 claims description 3
MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 claims description 2
YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 claims description 2
NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 claims description 2
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 claims description 2
239000004305 biphenyl Substances 0.000 claims description 2
AQNQQHJNRPDOQV-UHFFFAOYSA-N bromocyclohexane Chemical compound BrC1CCCCC1 AQNQQHJNRPDOQV-UHFFFAOYSA-N 0.000 claims description 2
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 claims description 2
AEILLAXRDHDKDY-UHFFFAOYSA-N bromomethylcyclopropane Chemical compound BrCC1CC1 AEILLAXRDHDKDY-UHFFFAOYSA-N 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 12
LOYZVRIHVZEDMW-UHFFFAOYSA-N 1-bromo-3-methylbut-2-ene Chemical compound CC(C)=CCBr LOYZVRIHVZEDMW-UHFFFAOYSA-N 0.000 claims 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
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DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
229910052744 lithium Inorganic materials 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 63
239000000203 mixture Substances 0.000 description 32
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238000003756 stirring Methods 0.000 description 9
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239000002244 precipitate Substances 0.000 description 5
HLLGFGBLKOIZOM-UHFFFAOYSA-N 2,2-diphenylacetaldehyde Chemical compound C=1C=CC=CC=1C(C=O)C1=CC=CC=C1 HLLGFGBLKOIZOM-UHFFFAOYSA-N 0.000 description 4
241000699666 Mus <mouse, genus> Species 0.000 description 4
241000700159 Rattus Species 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
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239000002250 absorbent Substances 0.000 description 4
230000002745 absorbent Effects 0.000 description 4
239000002585 base Substances 0.000 description 4
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235000019438 castor oil Nutrition 0.000 description 4
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ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 4
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229910000041 hydrogen chloride Inorganic materials 0.000 description 4
238000005984 hydrogenation reaction Methods 0.000 description 4
239000000155 melt Substances 0.000 description 4
230000007935 neutral effect Effects 0.000 description 4
239000012299 nitrogen atmosphere Substances 0.000 description 4
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239000011877 solvent mixture Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
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239000006286 aqueous extract Substances 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
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
229920000609 methyl cellulose Polymers 0.000 description 3
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MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
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RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
206010012735 Diarrhoea Diseases 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
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125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
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150000007522 mineralic acids Chemical class 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000004043 oxo group Chemical group O=* 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/12—Antidiarrhoeals

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Indole Compounds (AREA)

NO781333A 1977-04-18 1978-04-17 Fremgangsmaate til fremstilling av 2-(2,2-diarylalkyl)-1-azabicyklo(2.2.2)ocetan og beslektede forbindelser NO781333L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US05/788,189 US4125531A (en)	1977-04-18	1977-04-18	2-Substituted-1-azabicyclo[2.2.2]octanes

Publications (1)

Publication Number	Publication Date
NO781333L true NO781333L (no)	1978-10-19

Family

ID=25143721

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO781333A NO781333L (no)	1977-04-18	1978-04-17	Fremgangsmaate til fremstilling av 2-(2,2-diarylalkyl)-1-azabicyklo(2.2.2)ocetan og beslektede forbindelser

Country Status (19)

Country	Link
US (1)	US4125531A (de)
JP (1)	JPS53132596A (de)
AT (1)	AT357553B (de)
AU (1)	AU3516178A (de)
BE (1)	BE866031A (de)
DE (1)	DE2816633A1 (de)
DK (1)	DK166978A (de)
ES (1)	ES468874A1 (de)
FI (1)	FI781161A7 (de)
FR (1)	FR2387980A1 (de)
GB (1)	GB1569249A (de)
IE (1)	IE46737B1 (de)
IL (1)	IL54519A0 (de)
NL (1)	NL7804145A (de)
NO (1)	NO781333L (de)
NZ (1)	NZ186991A (de)
PT (1)	PT67910B (de)
SE (1)	SE7804307L (de)
ZA (1)	ZA782212B (de)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4203989A (en) *	1979-04-30	1980-05-20	G. D. Searle & Co.	Anti-diarrheal diaryl-(1-azabicyclo(2.2.2)octan-2-yl)-alkanols and related compounds
US4203990A (en) *	1979-04-30	1980-05-20	G. D. Searle & Co.	Anti-diarrheal 2-substituted quinuclidines
US4599344A (en) *	1984-10-31	1986-07-08	Schering A.G.	Quinuclidines and quinuclidinium salts as antiarrhythmic agents
EP0412798A3 (en) *	1989-08-08	1992-07-01	Merck Sharp & Dohme Ltd.	Substituted pyridines, their preparation, formulations and use in dementia
EP0499313B1 (de) *	1991-02-11	1997-06-11	MERCK SHARP & DOHME LTD.	Azabicyclische Verbindungen, diese enthaltende pharmazeutische Zubereitungen und ihre therapeutische Verwendung
US5962477A (en) *	1994-04-12	1999-10-05	Adolor Corporation	Screening methods for cytokine inhibitors
US6190691B1 (en)	1994-04-12	2001-02-20	Adolor Corporation	Methods for treating inflammatory conditions
US6573282B1 (en)	1995-09-12	2003-06-03	Adolor Corporation	Peripherally active anti-hyperalgesic opiates
US5849761A (en) *	1995-09-12	1998-12-15	Regents Of The University Of California	Peripherally active anti-hyperalgesic opiates
US6353004B1 (en)	1997-07-14	2002-03-05	Adolor Coporation	Peripherally acting anti-pruritic opiates
US5849762A (en) *	1997-07-14	1998-12-15	Adolor Corporation	Peripherally acting anti-pruritic opiates
CA2811272C (en)	2003-04-08	2016-12-20	Progenics Pharmaceuticals, Inc.	Pharmaceutical formulations containing methylnaltrexone
AR057035A1 (es)	2005-05-25	2007-11-14	Progenics Pharm Inc	SíNTESIS DE (R)-N-METILNALTREXONA, COMPOSICIONES FARMACÉUTICAS Y USOS
AR057325A1 (es)	2005-05-25	2007-11-28	Progenics Pharm Inc	Sintesis de (s)-n-metilnaltrexona, composiciones farmaceuticas y usos
TWI489984B (zh)	2006-08-04	2015-07-01	Wyeth Corp	用於非經腸道傳輸化合物之配方及其用途
EP2565195B1 (de)	2007-03-29	2015-05-06	Wyeth LLC	Peripherer Opioid-Rezeptor sowie Antagonisten und Verwendungen davon
PL2137191T3 (pl)	2007-03-29	2016-12-30		Antagoniści obwodowego receptora opioidowego i ich zastosowania
JP2010522756A (ja)	2007-03-29	2010-07-08	プロジェニックスファーマシューティカルズ，インコーポレーテッド	結晶形およびその使用
AU2008349873B2 (en)	2008-02-06	2014-02-13	Progenics Pharmaceuticals, Inc.	Preparation and use of (R),(R)-2,2'-bis-methylnaltrexone
CA2676881C (en)	2008-09-30	2017-04-25	Wyeth	Peripheral opioid receptor antagonists and uses thereof
CN110372571B (zh)	2018-04-12	2022-11-15	中国科学院大连化学物理研究所	一种2-(2,2-二芳基乙基)-环胺衍生物或盐及合成和应用与组合物

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3506672A (en) *	1968-03-29	1970-04-14	Aldrich Chem Co Inc	2-(4,4'-dihalo)-benzhydryl-3-quinuclidinols
SU495310A1 (ru) *	1974-03-05	1975-12-15	Всесоюзный Научно-Исследовательский Химико-Фармацевтический Институт Им.С.Орджоникидзе	Хинуклидил-3-диарал(гетерил) карбинолы, про вл ющие антигистаминную, антисеротониновую и антиаллергическую активность и способ их получени
US4013667A (en) *	1976-03-08	1977-03-22	G. D. Searle & Co.	2,2-Diaryl-3-(1-azabicyclo[2.2.2]oct-2-yl)propionamides and intermediates thereto

1977
- 1977-04-18 US US05/788,189 patent/US4125531A/en not_active Expired - Lifetime
1978
- 1978-04-17 DK DK166978A patent/DK166978A/da not_active IP Right Cessation
- 1978-04-17 ES ES468874A patent/ES468874A1/es not_active Expired
- 1978-04-17 BE BE186827A patent/BE866031A/xx unknown
- 1978-04-17 SE SE7804307A patent/SE7804307L/xx unknown
- 1978-04-17 IL IL54519A patent/IL54519A0/xx unknown
- 1978-04-17 AU AU35161/78A patent/AU3516178A/en active Pending
- 1978-04-17 NZ NZ186991A patent/NZ186991A/xx unknown
- 1978-04-17 FI FI781161A patent/FI781161A7/fi not_active Application Discontinuation
- 1978-04-17 NO NO781333A patent/NO781333L/no unknown
- 1978-04-17 DE DE19782816633 patent/DE2816633A1/de not_active Withdrawn
- 1978-04-17 IE IE745/78A patent/IE46737B1/en unknown
- 1978-04-17 AT AT266178A patent/AT357553B/de not_active IP Right Cessation
- 1978-04-17 PT PT67910A patent/PT67910B/pt unknown
- 1978-04-17 GB GB14965/78A patent/GB1569249A/en not_active Expired
- 1978-04-18 FR FR7811370A patent/FR2387980A1/fr not_active Withdrawn
- 1978-04-18 ZA ZA00782212A patent/ZA782212B/xx unknown
- 1978-04-18 NL NL7804145A patent/NL7804145A/xx not_active Application Discontinuation
- 1978-04-18 JP JP4578878A patent/JPS53132596A/ja active Pending

Also Published As

Publication number	Publication date
AU3516178A (en)	1979-10-25
ZA782212B (en)	1979-11-28
DK166978A (da)	1978-10-19
SE7804307L (sv)	1978-10-19
IL54519A0 (en)	1978-07-31
PT67910A (en)	1978-05-01
BE866031A (fr)	1978-10-17
PT67910B (en)	1979-11-14
NL7804145A (nl)	1978-10-20
AT357553B (de)	1980-07-25
ATA266178A (de)	1979-12-15
NZ186991A (en)	1979-12-11
FR2387980A1 (fr)	1978-11-17
GB1569249A (en)	1980-06-11
JPS53132596A (en)	1978-11-18
IE46737B1 (en)	1983-09-07
FI781161A7 (fi)	1978-10-19
IE780745L (en)	1978-10-18
DE2816633A1 (de)	1978-10-19
US4125531A (en)	1978-11-14
ES468874A1 (es)	1978-12-01

Publication	Publication Date	Title
NO781333L (no)	1978-10-19	Fremgangsmaate til fremstilling av 2-(2,2-diarylalkyl)-1-azabicyklo(2.2.2)ocetan og beslektede forbindelser
NO884835L (no)	1989-05-02	Fremgangsmaate for fremstilling av terapeutisk aktive tetrahydro-furo-og-tieno (2,3.-c)pyridiner.
NO141487B (no)	1979-12-10	Traadloest informasjonstransmisjonssystem
JPS591711B2 (ja)	1984-01-13	５−テノイルピロ−ル酢酸誘導体の製造法
NO168795B (no)	1991-12-23	Fiberoptisk undervannsledning for telekommunikasjonsformaal
DE2814556A1 (de)	1978-10-12	Substituierte phenylessigsaeurederivate und verfahren zu deren herstellung
DK162629B (da)	1991-11-25	2-substituerede 1-aralkyl-imidazoler og farmaceutiske midler der indeholder disse, anvendelse heraf til fremstilling af farmaceutiske midler samt fremgangsmaade til fremstilling heraf
NO152091B (no)	1985-04-22	Analogifremgangsmaate ved fremstilling av antiinflammatorisk virksomme 5-substituerte 2,3-difenylthiofener
JPS6253504B2 (de)	1987-11-10
US3067101A (en)	1962-12-04	Method for controlling hypertension
NO761304L (de)	1976-10-19
Maccarone et al.	1974	Leaving group effect in the reaction of 2-thiophenesulfonyl halides with anilines in methanol
NO127149B (de)	1973-05-14
JPS6054285B2 (ja)	1985-11-29	シクロヘキサン誘導体を含有する医薬
NO821192L (no)	1982-10-15	Fremgangsmaate for fremstilling av fenetanolaminer.
NO760116L (de)	1976-07-16
PT85477B (pt)	1990-06-29	Processo para a preparacao de derivados heterociclicos substituidos de fenil butenamida
DE1620438A1 (de)	1970-04-23	Verfahren zur Herstellung neuer Diazabicyclo-(4,4,0)-decanderivate
US4013667A (en)	1977-03-22	2,2-Diaryl-3-(1-azabicyclo[2.2.2]oct-2-yl)propionamides and intermediates thereto
Campaigne et al.	1953	3-Substituted Thiophenes. V. Alkamine Esters of Phenyl-3-thienylglycolic Acid1
US3420841A (en)	1969-01-07	1,3-di-(4-pyridyl)propane derivatives
KR830001838B1 (ko)	1983-09-14	페닐-퀴놀리지딘의 제조방법
IE44449B1 (en)	1981-12-02	11-methylene-6-piperazinyl-morphanthridine derivatives
NO780100L (no)	1978-07-13	Fremgangsmaate til fremstilling av (1,1-ditienyl-(3)-1-hydroksy-propyl-(3))-(1-fenyl-1-hydroksy-propyl-(2))-amin og (1. ,1-ditienyl-(3-propen-(1)-yl-(3))-(1-fenyl-propyl-(2))-amin
NO137893B (no)	1978-02-06	Analogifremgangsm}te for fremstilling av terapeutisk aktive 1-m-trifluormetylfenyl-2-cyanoalkylaminopropaner