NO983990L - Aminotetralin-derivater og blandinger og metode for anvendelse derav - Google Patents

Aminotetralin-derivater og blandinger og metode for anvendelse derav Download PDF

Info

Publication number: NO983990L
Authority: NO; Norway
Prior art keywords: methyl; amino; hydrogen; mmol; compound
Prior art date: 1996-03-01

Application number

NO983990A

Other languages

English (en)

Norwegian (no)

Other versions

NO983990D0 (no

Inventor

Edward John Warawa

Bernard Migler

Original Assignee

Zeneca Ltd

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.)

1996-03-01

Filing date

1998-08-31

Publication date

1998-08-31

1998-08-31 Application filed by Zeneca Ltd filed Critical Zeneca Ltd

1998-08-31 Publication of NO983990D0 publication Critical patent/NO983990D0/no

1998-08-31 Publication of NO983990L publication Critical patent/NO983990L/no

Links

238000000034 method Methods 0.000 title claims abstract description 41
JRZGPXSSNPTNMA-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalen-1-amine Chemical class C1=CC=C2C(N)CCCC2=C1 JRZGPXSSNPTNMA-UHFFFAOYSA-N 0.000 title abstract description 6
239000000203 mixture Substances 0.000 title description 31
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 37
239000001257 hydrogen Substances 0.000 claims abstract description 37
150000003839 salts Chemical class 0.000 claims abstract description 31
150000002431 hydrogen Chemical group 0.000 claims abstract description 27
238000011282 treatment Methods 0.000 claims abstract description 27
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 24
229910052736 halogen Inorganic materials 0.000 claims abstract description 22
150000002367 halogens Chemical group 0.000 claims abstract description 22
208000016285 Movement disease Diseases 0.000 claims abstract description 17
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 14
230000002265 prevention Effects 0.000 claims abstract 2
150000001875 compounds Chemical class 0.000 claims description 120
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 35
125000000217 alkyl group Chemical group 0.000 claims description 20
-1 methoxy, ethoxy Chemical group 0.000 claims description 20
239000002253 acid Substances 0.000 claims description 18
125000003545 alkoxy group Chemical group 0.000 claims description 13
WWRJRKPCRXJACI-JTQLQIEISA-N (2s)-8-methoxy-n-methyl-1,2,3,4-tetrahydronaphthalen-2-amine Chemical compound C1=CC(OC)=C2C[C@@H](NC)CCC2=C1 WWRJRKPCRXJACI-JTQLQIEISA-N 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
239000003638 chemical reducing agent Substances 0.000 claims description 8
239000007788 liquid Substances 0.000 claims description 8
125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 8
PMZSOOOPRABQMS-FVGYRXGTSA-N (2s)-5,8-dimethoxy-n-methyl-1,2,3,4-tetrahydronaphthalen-2-amine;hydrochloride Chemical compound Cl.COC1=CC=C(OC)C2=C1C[C@@H](NC)CC2 PMZSOOOPRABQMS-FVGYRXGTSA-N 0.000 claims description 6
206010043118 Tardive Dyskinesia Diseases 0.000 claims description 6
239000003814 drug Substances 0.000 claims description 6
ZSIAKNKANPQFTH-PPHPATTJSA-N (2s)-8-methoxy-n-methyl-1,2,3,4-tetrahydronaphthalen-2-amine;hydrochloride Chemical compound Cl.C1=CC(OC)=C2C[C@@H](NC)CCC2=C1 ZSIAKNKANPQFTH-PPHPATTJSA-N 0.000 claims description 5
239000000654 additive Substances 0.000 claims description 5
239000003085 diluting agent Substances 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
239000000825 pharmaceutical preparation Substances 0.000 claims description 4
CKXFPBHAUKEBBF-PPHPATTJSA-N (2s)-n-ethyl-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-amine;hydrochloride Chemical compound Cl.C1=CC(OC)=C2C[C@@H](NCC)CCC2=C1OC CKXFPBHAUKEBBF-PPHPATTJSA-N 0.000 claims description 3
PMZSOOOPRABQMS-UHFFFAOYSA-N 5,8-dimethoxy-n-methyl-1,2,3,4-tetrahydronaphthalen-2-amine;hydrochloride Chemical compound Cl.COC1=CC=C(OC)C2=C1CC(NC)CC2 PMZSOOOPRABQMS-UHFFFAOYSA-N 0.000 claims description 3
AAFPRLDUYSCCGD-UHFFFAOYSA-N 5-bromo-8-methoxy-n-methyl-1,2,3,4-tetrahydronaphthalen-2-amine;hydrochloride Chemical compound Cl.C1=CC(OC)=C2CC(NC)CCC2=C1Br AAFPRLDUYSCCGD-UHFFFAOYSA-N 0.000 claims description 3
LYMDZJCFPOOCBO-UHFFFAOYSA-N 5-ethoxy-8-methoxy-n-methyl-1,2,3,4-tetrahydronaphthalen-2-amine;hydrochloride Chemical compound Cl.C1C(NC)CCC2=C1C(OC)=CC=C2OCC LYMDZJCFPOOCBO-UHFFFAOYSA-N 0.000 claims description 3
BJFHJWRQUZEHRE-UHFFFAOYSA-N 6-bromo-5,8-dimethoxy-n-methyl-1,2,3,4-tetrahydronaphthalen-2-amine;hydrochloride Chemical compound Cl.COC1=CC(Br)=C(OC)C2=C1CC(NC)CC2 BJFHJWRQUZEHRE-UHFFFAOYSA-N 0.000 claims description 3
ZSIAKNKANPQFTH-UHFFFAOYSA-N 8-methoxy-n-methyl-1,2,3,4-tetrahydronaphthalen-2-amine;hydrochloride Chemical compound Cl.C1=CC(OC)=C2CC(NC)CCC2=C1 ZSIAKNKANPQFTH-UHFFFAOYSA-N 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
CKXFPBHAUKEBBF-UHFFFAOYSA-N n-ethyl-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-amine;hydrochloride Chemical compound Cl.C1=CC(OC)=C2CC(NCC)CCC2=C1OC CKXFPBHAUKEBBF-UHFFFAOYSA-N 0.000 claims description 3
125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 claims 2
230000000996 additive effect Effects 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 146
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 109
239000000243 solution Substances 0.000 description 74
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 65
239000002904 solvent Substances 0.000 description 54
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 51
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LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 45
239000007787 solid Substances 0.000 description 41
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 38
239000000047 product Substances 0.000 description 31
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HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
239000012267 brine Substances 0.000 description 21
239000000460 chlorine Substances 0.000 description 21
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 21
241000282693 Cercopithecidae Species 0.000 description 20
229910052943 magnesium sulfate Inorganic materials 0.000 description 19
235000019341 magnesium sulphate Nutrition 0.000 description 19
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 18
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 18
230000002829 reductive effect Effects 0.000 description 18
238000002360 preparation method Methods 0.000 description 17
238000003756 stirring Methods 0.000 description 17
238000012360 testing method Methods 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
238000001035 drying Methods 0.000 description 15
239000007858 starting material Substances 0.000 description 15
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
238000001914 filtration Methods 0.000 description 14
239000012279 sodium borohydride Substances 0.000 description 14
229910000033 sodium borohydride Inorganic materials 0.000 description 14
238000004809 thin layer chromatography Methods 0.000 description 14
230000017311 musculoskeletal movement, spinal reflex action Effects 0.000 description 13
239000003960 organic solvent Substances 0.000 description 13
239000011734 sodium Substances 0.000 description 13
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
239000012230 colorless oil Substances 0.000 description 12
239000002244 precipitate Substances 0.000 description 12
229910000085 borane Inorganic materials 0.000 description 11
208000015592 Involuntary movements Diseases 0.000 description 10
150000001412 amines Chemical class 0.000 description 10
238000004458 analytical method Methods 0.000 description 10
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 10
238000004821 distillation Methods 0.000 description 10
230000000142 dyskinetic effect Effects 0.000 description 10
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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 9
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 9
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239000011630 iodine Substances 0.000 description 9
229910052740 iodine Inorganic materials 0.000 description 9
LCGFVWKNXLRFIF-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalen-2-amine Chemical class C1=CC=C2CC(N)CCC2=C1 LCGFVWKNXLRFIF-UHFFFAOYSA-N 0.000 description 7
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VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 7
229960004046 apomorphine Drugs 0.000 description 7
239000012458 free base Substances 0.000 description 7
229910052757 nitrogen Inorganic materials 0.000 description 7
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 7
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
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JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000002895 organic esters Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000002304 perfume Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000006187 pill Substances 0.000 description 1
230000005371 pilomotor reflex Effects 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
230000036544 posture Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000000246 remedial effect Effects 0.000 description 1
238000007142 ring opening reaction Methods 0.000 description 1
208000026451 salivation Diseases 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
235000003441 saturated fatty acids Nutrition 0.000 description 1
150000004671 saturated fatty acids Chemical class 0.000 description 1
238000007790 scraping Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910001961 silver nitrate Inorganic materials 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000003491 tear gas Substances 0.000 description 1
238000010998 test method Methods 0.000 description 1
125000004862 thiobutyl group Chemical group 0.000 description 1
125000004014 thioethyl group Chemical group [H]SC([H])([H])C([H])([H])* 0.000 description 1
125000004035 thiopropyl group Chemical group [H]SC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229960002784 thioridazine Drugs 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 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
238000001665 trituration Methods 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/74—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with rings other than six-membered aromatic rings being part of the carbon skeleton
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Neurosurgery (AREA)
Life Sciences & Earth Sciences (AREA)
Neurology (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Psychology (AREA)
Pharmacology & Pharmacy (AREA)
Biomedical Technology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Peptides Or Proteins (AREA)

NO983990A 1996-03-01 1998-08-31 Aminotetralin-derivater og blandinger og metode for anvendelse derav NO983990L (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US1264096P	1996-03-01	1996-03-01
PCT/GB1997/000516 WO1997031887A1 (en)	1996-03-01	1997-02-25	Aminotetralin derivatives and compositions and method of use thereof

Publications (2)

Publication Number	Publication Date
NO983990D0 NO983990D0 (no)	1998-08-31
NO983990L true NO983990L (no)	1998-08-31

Family

ID=21755962

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO983990A NO983990L (no)	1996-03-01	1998-08-31	Aminotetralin-derivater og blandinger og metode for anvendelse derav

Country Status (14)

Country	Link
US (1)	US5807897A (de)
EP (1)	EP0883599B1 (de)
JP (1)	JP4083221B2 (de)
KR (1)	KR19990087369A (de)
CN (1)	CN1212682A (de)
AT (1)	ATE218535T1 (de)
AU (1)	AU733264B2 (de)
DE (1)	DE69713067T2 (de)
IL (1)	IL125907A0 (de)
NO (1)	NO983990L (de)
NZ (1)	NZ330974A (de)
TW (1)	TW409113B (de)
WO (1)	WO1997031887A1 (de)
ZA (1)	ZA971670B (de)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9726736D0 (en)	1997-12-18	1998-02-18	Zeneca Ltd	Chemical compounds
GB9914015D0 (en) *	1999-06-17	1999-08-18	Zeneca Ltd	Chemical compounds
EP1140863A1 (de) *	1998-12-24	2001-10-10	AstraZeneca AB	1,4-diazacycloheptanderivate nützlich zur behandlung von neurologische störungen
GB9914025D0 (en) *	1999-06-17	1999-08-18	Zeneca Ltd	Chemical compounds
GB9914024D0 (en) *	1999-06-17	1999-08-18	Zeneca Ltd	Chemical compounds
PL1658277T3 (pl) *	2003-08-18	2012-10-31	H Lundbeck As	Sól bursztynianowa i malonianowa trans-4-((1R,3S)-6-chloro-3-fenyloindan-1-ylo)-1,2,2-tri-metylopiperazyny i zastosowanie jako lek
TWI376373B (en) *	2005-02-16	2012-11-11	Lundbeck & Co As H	Crystalline base of a pharmaceutical compound
TWI453198B (zh) *	2005-02-16	2014-09-21	Lundbeck & Co As H	製造反式-1-((1r,3s)-6-氯基-3-苯基茚滿-1-基) -3 , 3 -二甲基六氫吡與其鹽類之方法及製造4-((1r , 3s）-6 -氯基-3-苯基茚滿-1-基 )-1,2,2-三甲基六氫吡與其鹽類之方法
CN102065861B (zh) *	2008-05-07	2013-10-16	H.隆德贝克有限公司	反式-4-((1r，3s)-6-氯-3-苯基茚满-1-基)-1，2，2-三甲基哌嗪用于改善认知的用途
CN102170884A (zh) *	2008-10-03	2011-08-31	H.隆德贝克有限公司	口服制剂
MX2023014630A (es)	2021-06-08	2024-01-30	Atai Therapeutics Inc	Activadores de dimetoxifenilalquilamina de receptores de serotonina.
EP4457203A4 (de) *	2021-12-27	2025-12-17	Atai Therapeutics Inc	Aminotetralin-aktivatoren von serotoninrezeptoren
US12343319B2 (en)	2023-05-01	2025-07-01	Atai Therapeutics, Inc.	Compositions and methods for treatment of diseases and disorders

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4320148A (en) *	1980-11-24	1982-03-16	Smithkline Corporation	2-Aminotetralin compounds, pharmaceutical compositions and method of producing central alpha1 agonist activity
US5225596A (en) *	1989-01-09	1993-07-06	The Upjohn Company	Halo substituted aminotetralins
SE8904127D0 (sv) *	1989-12-07	1989-12-07	Astra Ab	New biocyclic amino-substituted compounds
EP0450238A1 (de) *	1990-03-30	1991-10-09	Merrell Dow Pharmaceuticals Inc.	Verbindungen für die Behandlung von Migräne

1997
- 1997-02-21 US US08/804,195 patent/US5807897A/en not_active Expired - Lifetime
- 1997-02-25 CN CN97192657A patent/CN1212682A/zh active Pending
- 1997-02-25 IL IL12590797A patent/IL125907A0/xx unknown
- 1997-02-25 JP JP53069697A patent/JP4083221B2/ja not_active Expired - Fee Related
- 1997-02-25 KR KR1019980706779A patent/KR19990087369A/ko not_active Withdrawn
- 1997-02-25 NZ NZ330974A patent/NZ330974A/xx unknown
- 1997-02-25 DE DE69713067T patent/DE69713067T2/de not_active Expired - Lifetime
- 1997-02-25 AT AT97905261T patent/ATE218535T1/de not_active IP Right Cessation
- 1997-02-25 AU AU18879/97A patent/AU733264B2/en not_active Ceased
- 1997-02-25 WO PCT/GB1997/000516 patent/WO1997031887A1/en not_active Ceased
- 1997-02-25 EP EP97905261A patent/EP0883599B1/de not_active Expired - Lifetime
- 1997-02-26 ZA ZA9701670A patent/ZA971670B/xx unknown
- 1997-02-26 TW TW086102356A patent/TW409113B/zh not_active IP Right Cessation
1998
- 1998-08-31 NO NO983990A patent/NO983990L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
TW409113B (en)	2000-10-21
WO1997031887A1 (en)	1997-09-04
EP0883599A1 (de)	1998-12-16
JP4083221B2 (ja)	2008-04-30
NZ330974A (en)	2000-05-26
AU733264B2 (en)	2001-05-10
KR19990087369A (ko)	1999-12-27
CN1212682A (zh)	1999-03-31
DE69713067D1 (de)	2002-07-11
NO983990D0 (no)	1998-08-31
ZA971670B (en)	1997-09-01
ATE218535T1 (de)	2002-06-15
DE69713067T2 (de)	2002-12-19
IL125907A0 (en)	1999-04-11
AU1887997A (en)	1997-09-16
JP2000506137A (ja)	2000-05-23
EP0883599B1 (de)	2002-06-05
US5807897A (en)	1998-09-15

Legal Events

Date	Code	Title	Description
2002-04-08	FC2A	Withdrawal, rejection or dismissal of laid open patent application

Publication	Publication Date	Title
DK172103B1 (da)	1997-10-27	Hidtil ukendte 3,3-difenylpropylaminer, farmaceutiske præparater indeholdende disse, deres anvendelse til fremstilling af et anticholinergt lægemiddel samt fremgangsmåde til deres fremstilling
NO983990L (no)	1998-08-31	Aminotetralin-derivater og blandinger og metode for anvendelse derav
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US20070299091A1 (en)	2007-12-27	Azaindole Carboxamides
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CA3213289A1 (en)	2022-09-15	Phenalkylamines and methods of making and using the same
DE69935331T2 (de)	2007-10-31	Verfahren und verbindungen zur behandlung der depression
KR20090079984A (ko)	2009-07-22	신규 아릴비시클로[3.1.0]헥실아민 및 이의 제조 및 사용을 위한 방법 및 조성물
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CN101119983B (zh)	2014-11-12	反式-1-((1r,3s)-6-氯-3-苯基茚满-1-基)-3,3-二甲基哌嗪的结晶碱
PL141501B1 (en)	1987-07-31	Method of obtaining novel derivatives of quinoline and indene
KOJIMA et al.	1985	Syntheses of (±)-2-[(inden-7-yloxy) methyl] morpholine hydrochloride (YM-08054, indeloxazine hydrochloride) and its derivatives with potential cerebral-activating and antidepressive properties
CN100441188C (zh)	2008-12-10	作为mao－b抑制剂的苯并氮杂衍生物
FI67700C (fi)	1985-05-10	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara fenyl-kinolizidiner
CH636076A5 (de)	1983-05-13	Benzylalkoholderivate und verfahren zu deren herstellung.
PL215451B1 (pl)	2013-12-31	Epoksydowe pochodne alkaloidów drzewa chinowego i sposób wytwarzania epoksydowych pochodnych alkaloidów drzewa chinowego
DE60305717T2 (de)	2007-05-03	Benzylmorpholinderivate
MXPA98007074A (en)	1999-02-24	Derivatives of aminotetralin and compositions and method for using mis
CA2243243A1 (en)	1997-09-04	Aminotetralin derivatives and compositions and method of use thereof
EP0097628B1 (de)	1990-09-19	Piperidinderivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate
JP3888397B2 (ja)	2007-02-28	イソプレン誘導体
EP0116372B1 (de)	1987-01-21	2H-(1)Benzoxepino(5,4-b)-1,4-oxazinderivate
EP0090526A1 (de)	1983-10-05	Substituierte Dodecahydrotriphenylene, Decahydro-1H-cyclopentaphenanthrene, Decahydro-1H-pyridophenanthridine und Decahydropyrrolo(1,2-f)phenanthridine mit Wirkung auf das Zentralnervensystem
EP0265388A1 (de)	1988-04-27	Pyrrol-Derivate, therapeutische Mittel, die sie enthalten und ihre Verwendung