HU184624B - Process for preparing amino-substituted 4,5,6,7-tetrahydro-1h/or 2h/-indazole derivatives - Google Patents

Process for preparing amino-substituted 4,5,6,7-tetrahydro-1h/or 2h/-indazole derivatives Download PDF

Info

Publication number: HU184624B
Authority: HU; Hungary
Prior art keywords: tetrahydro; indazole; amino; compounds; propyl
Prior art date: 1979-01-22

Application number

HU79EI862A

Other languages

English (en)

Hungarian (hu)

Inventor

Nicholas J Bach

Edmunkd C Kornfeld

Original Assignee

Lilly Co Eli

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.)

1979-01-22

Filing date

1979-06-26

Publication date

1984-09-28

1979-06-26 Application filed by Lilly Co Eli filed Critical Lilly Co Eli

1984-09-28 Publication of HU184624B publication Critical patent/HU184624B/hu

Links

125000003277 amino group Chemical group 0.000 title claims description 3
238000004519 manufacturing process Methods 0.000 title claims description 3
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 15
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims description 44
239000001257 hydrogen Substances 0.000 claims description 16
229910052739 hydrogen Inorganic materials 0.000 claims description 16
-1 (n-propylamino) - 4,5,6,7-tetrahydro-1H-indazole Chemical compound 0.000 claims description 14
238000002360 preparation method Methods 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 11
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 10
238000000034 method Methods 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims description 9
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
229910052987 metal hydride Inorganic materials 0.000 claims description 7
150000004681 metal hydrides Chemical class 0.000 claims description 7
239000003638 chemical reducing agent Substances 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 5
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UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
229940043376 ammonium acetate Drugs 0.000 description 2
235000019257 ammonium acetate Nutrition 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
230000037396 body weight Effects 0.000 description 2
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125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
238000002347 injection Methods 0.000 description 2
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VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
239000000463 material Substances 0.000 description 2
229940098779 methanesulfonic acid Drugs 0.000 description 2
QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
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150000003335 secondary amines Chemical class 0.000 description 2
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NYOWYNSNCXRVNQ-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1h-indazole Chemical class C1=CCC2CNNC2=C1 NYOWYNSNCXRVNQ-UHFFFAOYSA-N 0.000 description 1
HCSBTDBGTNZOAB-UHFFFAOYSA-N 2,3-dinitrobenzoic acid Chemical compound OC(=O)C1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O HCSBTDBGTNZOAB-UHFFFAOYSA-N 0.000 description 1
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238000007912 intraperitoneal administration Methods 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
ZDGGJQMSELMHLK-UHFFFAOYSA-N m-Trifluoromethylhippuric acid Chemical compound OC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 ZDGGJQMSELMHLK-UHFFFAOYSA-N 0.000 description 1
IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
125000005341 metaphosphate group Chemical group 0.000 description 1
IZYBEMGNIUSSAX-UHFFFAOYSA-N methyl benzenecarboperoxoate Chemical compound COOC(=O)C1=CC=CC=C1 IZYBEMGNIUSSAX-UHFFFAOYSA-N 0.000 description 1
229940095102 methyl benzoate Drugs 0.000 description 1
XCVNDBIXFPGMIW-UHFFFAOYSA-N n-ethylpropan-1-amine Chemical group CCCNCC XCVNDBIXFPGMIW-UHFFFAOYSA-N 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
210000001577 neostriatum Anatomy 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
DIVDFFZHCJEHGG-UHFFFAOYSA-N oxidopamine Chemical compound NCCC1=CC(O)=C(O)C=C1O DIVDFFZHCJEHGG-UHFFFAOYSA-N 0.000 description 1
235000019371 penicillin G benzathine Nutrition 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
DYUMLJSJISTVPV-UHFFFAOYSA-N phenyl propanoate Chemical compound CCC(=O)OC1=CC=CC=C1 DYUMLJSJISTVPV-UHFFFAOYSA-N 0.000 description 1
229940049953 phenylacetate Drugs 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
229950009215 phenylbutanoic acid Drugs 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
229940080818 propionamide Drugs 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
UORVCLMRJXCDCP-UHFFFAOYSA-M propynoate Chemical compound [O-]C(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-M 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000005932 reductive alkylation reaction Methods 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
229940116351 sebacate Drugs 0.000 description 1
CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
238000009987 spinning Methods 0.000 description 1
238000012453 sprague-dawley rat model Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
TYFQFVWCELRYAO-UHFFFAOYSA-L suberate(2-) Chemical compound [O-]C(=O)CCCCCCC([O-])=O TYFQFVWCELRYAO-UHFFFAOYSA-L 0.000 description 1
210000003523 substantia nigra Anatomy 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
229940071104 xylenesulfonate Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles

Landscapes

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

HU79EI862A 1979-01-22 1979-06-26 Process for preparing amino-substituted 4,5,6,7-tetrahydro-1h/or 2h/-indazole derivatives HU184624B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US506479A	1979-01-22	1979-01-22

Publications (1)

Publication Number	Publication Date
HU184624B true HU184624B (en)	1984-09-28

Family

ID=21713977

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HU79EI862A HU184624B (en)	1979-01-22	1979-06-26	Process for preparing amino-substituted 4,5,6,7-tetrahydro-1h/or 2h/-indazole derivatives

Country Status (6)

Country	Link
JP (1)	JPS55100367A (cs)
KR (2)	KR830000708B1 (cs)
CS (1)	CS241020B2 (cs)
HU (1)	HU184624B (cs)
PL (2)	PL118568B1 (cs)
SU (3)	SU1311620A3 (cs)

1979
- 1979-06-26 HU HU79EI862A patent/HU184624B/hu not_active IP Right Cessation
- 1979-06-28 SU SU792786155A patent/SU1311620A3/ru active
- 1979-06-28 JP JP8340779A patent/JPS55100367A/ja active Pending
- 1979-06-28 CS CS794476A patent/CS241020B2/cs unknown
- 1979-06-29 KR KR1019790002148A patent/KR830000708B1/ko not_active Expired
- 1979-06-29 PL PL1979226403A patent/PL118568B1/pl unknown
- 1979-06-29 PL PL1979226402A patent/PL118459B1/pl unknown
- 1979-06-29 KR KR1019790002150A patent/KR830000754B1/ko not_active Expired
1981
- 1981-01-20 SU SU813230702A patent/SU976848A3/ru active
- 1981-01-21 SU SU813233699A patent/SU1015823A3/ru active

Also Published As

Publication number	Publication date
PL118568B1 (en)	1981-10-31
SU976848A3 (ru)	1982-11-23
PL118459B1 (en)	1981-10-31
KR830000754B1 (ko)	1983-04-09
CS241020B2 (en)	1986-03-13
SU1311620A3 (ru)	1987-05-15
JPS55100367A (en)	1980-07-31
KR830000708B1 (ko)	1983-04-06
SU1015823A3 (ru)	1983-04-30
CS447679A2 (en)	1985-06-13

Legal Events

Date	Code	Title	Description
1990-06-28	HU90	Patent valid on 900628
1991-05-28	HMM4	Cancellation of final prot. due to non-payment of fee

Publication	Publication Date	Title
KR0132903B1 (ko)	1998-04-17	축합 피자진 유도체
JP2716146B2 (ja)	1998-02-18	縮合インドール誘導体およびその製造方法
JPH0655728B2 (ja)	1994-07-27	ヒスタミン誘導体及びその製造方法並びに該誘導体を含有する医薬
HUP9904623A2 (hu)	2000-06-28	1H-Pirido[3,4-b]indol-4-karboxamid-származékok,eljárás előállításukra és alkalmazásuk a gyógyászatban
HU198713B (en)	1989-11-28	Process for producing ergolin derivatives and pharmaceutical compositions containing them as active components
HU206872B (en)	1993-01-28	Process for producing condensed pyrazolo-3-oxo-propiono-nitril derivatives and pharmaceutical compositions containing them
HK78895A (en)	1995-05-26	Substituted 1H-imidazoles
LU85725A1 (fr)	1985-10-22	Nouvelles 8alpha-acylaminoergolines,leur preparation et leur utilisation comme medicaments
CA2048959C (en)	2003-07-29	3-(1,2-benzisoxazol-3-yl)-4-pyridinamines and derivatives
EP0013789B1 (en)	1983-02-02	Amino-substituted 4,5,6,7-tetrahydro-1h (or 2h)-indazoles, their preparation and pharmaceutical compositions containing them
US4322540A (en)	1982-03-30	Substituted 4,5,6,7-tetrahydro-1H (or 2H)-indazoles
US4322430A (en)	1982-03-30	Amino-substituted 4,5,6,7-tetrahydro-1H (or 2H)-indazoles
JPH04247079A (ja)	1992-09-03	３−（１ｈ−インダゾール−３−イル）−４−ピリジンアミンおよびその製造法
US4477465A (en)	1984-10-16	Substituted 4,10-dihydro-10-oxothieno benzoxepins
FR2508457A1 (fr)	1982-12-31	Pyrrolo(2,1-b)quinazolines et pyrido(2,1-b)quinazolines substituees, leur preparation et leurs utilisations therapeutiques
JPS60226878A (ja)	1985-11-12	３−アミノ−１−（４，５，６，７−テトラヒドロベンゾチアゾリル）−２−ピラゾリン類およびその製法
CA1123842A (en)	1982-05-18	Amino-substituted 4,5,6,7-tetrahydro-1h (or 2h) - indazoles
KR830000708B1 (ko)	1983-04-06	아미노-치환된 4,5,6,7-테트라하이드로-1h(또는 2h)-인다졸의 제조방법
US4235776A (en)	1980-11-25	Tetrahydro-2H-benzo[c]pyrroles
JPS63196584A (ja)	1988-08-15	テトラヒドロピリド〔３′，４′：４，５〕ピロロ〔２，３−ｃ〕キノリン類
CA1128951A (en)	1982-08-03	Amino-substituted 4,5,6,7-tetrahydro-1h (or 2h)- indazoles
US5179100A (en)	1993-01-12	4,5-dihydropyrazolo[3,4-a]acridines
US4783464A (en)	1988-11-08	N-substituted ergoline- and 9,10-didehydro-ergoline-8-carboxamide-and-8-aminomethyl-derivatives, their production and their pharmaceutical composition
HU179973B (hu)	1983-01-28	Szabadalmi leírás
US4514411A (en)	1985-04-30	Substituted 4,10-dihydro-10-oxothieno benzoxepins