JPS6249267B2

JPS6249267B2 -

Info

Publication number: JPS6249267B2
Authority: JP; Japan
Prior art keywords: glycinamide; benzoyl; compound according; chlorophenyl; group
Prior art date: 1975-05-21
Legal status : Expired

Application number

JP51000465A

Other languages

English (en)

Japanese (ja)

Other versions

JPS51141848A (en

Inventor

Haabaato Hatsusaru Sedoritsuku

Henrii Jonson Uiriamu

Kureen Antonin

Aanesuto Sumisen Karee

Ansonii Tomasu Uiriamu

Current Assignee

F Hoffmann La Roche AG

Original Assignee

F Hoffmann La Roche AG

Priority date

1975-05-21

Filing date

1976-01-01

Publication date

1987-10-19

1976-01-01 Application filed by F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG

1976-12-07 Publication of JPS51141848A publication Critical patent/JPS51141848A/ja

1987-10-19 Publication of JPS6249267B2 publication Critical patent/JPS6249267B2/ja

Status Granted legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims description 74
239000000460 chlorine Substances 0.000 claims description 62
-1 hydroxyethyl group Chemical group 0.000 claims description 45
239000002253 acid Substances 0.000 claims description 32
BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 claims description 25
150000003839 salts Chemical class 0.000 claims description 21
125000000217 alkyl group Chemical group 0.000 claims description 20
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
125000002252 acyl group Chemical group 0.000 claims description 14
229940024606 amino acid Drugs 0.000 claims description 14
235000001014 amino acid Nutrition 0.000 claims description 14
150000001413 amino acids Chemical class 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 10
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 10
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 8
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
125000005059 halophenyl group Chemical group 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
239000004471 Glycine Substances 0.000 claims description 5
239000004472 Lysine Substances 0.000 claims description 5
VDKALJALMRQMMZ-NRFANRHFSA-N (2s)-2-amino-n-[2-(2-benzoyl-4-chloro-n-methylanilino)-2-oxoethyl]-3-phenylpropanamide Chemical compound C([C@H](N)C(=O)NCC(=O)N(C)C=1C(=CC(Cl)=CC=1)C(=O)C=1C=CC=CC=1)C1=CC=CC=C1 VDKALJALMRQMMZ-NRFANRHFSA-N 0.000 claims description 4
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 4
QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
229960000310 isoleucine Drugs 0.000 claims description 4
ZNWFDVCAVFZQNO-SFHVURJKSA-N (2s)-2-amino-n-[2-(2-benzoyl-4-chloro-n-methylanilino)-2-oxoethyl]-4-methylpentanamide Chemical compound CC(C)C[C@H](N)C(=O)NCC(=O)N(C)C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 ZNWFDVCAVFZQNO-SFHVURJKSA-N 0.000 claims description 3
FQLKUIGLPXMZIK-FQEVSTJZSA-N (2s)-2-amino-n-[2-(2-benzoyl-4-nitroanilino)-2-oxoethyl]-3-phenylpropanamide Chemical compound C([C@H](N)C(=O)NCC(=O)NC=1C(=CC(=CC=1)[N+]([O-])=O)C(=O)C=1C=CC=CC=1)C1=CC=CC=C1 FQLKUIGLPXMZIK-FQEVSTJZSA-N 0.000 claims description 3
OAEQXIARJNDJTL-UHFFFAOYSA-N 2-amino-n-[2-(2-benzoyl-4-chloro-n-methylanilino)-2-oxoethyl]acetamide Chemical compound NCC(=O)NCC(=O)N(C)C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 OAEQXIARJNDJTL-UHFFFAOYSA-N 0.000 claims description 3
NCVBBNHPRGOHFA-UHFFFAOYSA-N 2-amino-n-[2-[4-bromo-2-(pyridine-2-carbonyl)anilino]-2-oxoethyl]acetamide Chemical compound NCC(=O)NCC(=O)NC1=CC=C(Br)C=C1C(=O)C1=CC=CC=N1 NCVBBNHPRGOHFA-UHFFFAOYSA-N 0.000 claims description 3
ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims description 3
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 3
AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims description 3
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ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims description 3
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230000002921 anti-spasmodic effect Effects 0.000 claims description 3
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OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
239000004474 valine Substances 0.000 claims description 3
NVOGGKXDMDDFEG-HNNXBMFYSA-N (2s)-2,6-diamino-n-[2-[4-bromo-2-(pyridine-2-carbonyl)anilino]-2-oxoethyl]hexanamide Chemical compound NCCCC[C@H](N)C(=O)NCC(=O)NC1=CC=C(Br)C=C1C(=O)C1=CC=CC=N1 NVOGGKXDMDDFEG-HNNXBMFYSA-N 0.000 claims description 2
IWBMKDKUSRYYBX-LBPRGKRZSA-N (2s)-2-amino-n-[2-(2-benzoyl-4-chloro-n-methylanilino)-2-oxoethyl]propanamide Chemical compound C[C@H](N)C(=O)NCC(=O)N(C)C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 IWBMKDKUSRYYBX-LBPRGKRZSA-N 0.000 claims description 2
ZFIAFMFNIYHLTG-LBPRGKRZSA-N (2s)-2-amino-n-[2-(2-benzoyl-n-methyl-4-nitroanilino)-2-oxoethyl]propanamide Chemical compound C[C@H](N)C(=O)NCC(=O)N(C)C1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CC=CC=C1 ZFIAFMFNIYHLTG-LBPRGKRZSA-N 0.000 claims description 2
WJUAYYOOYTWICN-JTQLQIEISA-N (2s)-2-amino-n-[2-[4-bromo-2-(pyridine-2-carbonyl)anilino]-2-oxoethyl]propanamide Chemical compound C[C@H](N)C(=O)NCC(=O)NC1=CC=C(Br)C=C1C(=O)C1=CC=CC=N1 WJUAYYOOYTWICN-JTQLQIEISA-N 0.000 claims description 2
BGLIWPFJQFGODW-UHFFFAOYSA-N 2-amino-n-[2-(2-benzoyl-4-chloroanilino)-2-oxoethyl]acetamide Chemical compound NCC(=O)NCC(=O)NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 BGLIWPFJQFGODW-UHFFFAOYSA-N 0.000 claims description 2
HQMLIDZJXVVKCW-REOHCLBHSA-N L-alaninamide Chemical compound C[C@H](N)C(N)=O HQMLIDZJXVVKCW-REOHCLBHSA-N 0.000 claims description 2
101000655609 Streptomyces azureus Thiostrepton Proteins 0.000 claims description 2
MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 claims description 2
239000003158 myorelaxant agent Substances 0.000 claims description 2
MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims 2
239000004475 Arginine Substances 0.000 claims 2
WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims 2
ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims 2
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 2
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COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims 2
MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims 2
235000004279 alanine Nutrition 0.000 claims 2
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235000013930 proline Nutrition 0.000 claims 2
125000004076 pyridyl group Chemical group 0.000 claims 2
235000004400 serine Nutrition 0.000 claims 2
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IBFWGVBHULRTQY-ZDUSSCGKSA-N (2s)-2-amino-5-[[2-[4-bromo-2-(pyridine-2-carbonyl)anilino]-2-oxoethyl]amino]-5-oxopentanoic acid Chemical compound OC(=O)[C@@H](N)CCC(=O)NCC(=O)NC1=CC=C(Br)C=C1C(=O)C1=CC=CC=N1 IBFWGVBHULRTQY-ZDUSSCGKSA-N 0.000 claims 1
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FYUPTROPMDKDPF-UHFFFAOYSA-N 2-amino-n-[2-(2-benzoyl-4-nitroanilino)-2-oxoethyl]acetamide Chemical compound NCC(=O)NCC(=O)NC1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CC=CC=C1 FYUPTROPMDKDPF-UHFFFAOYSA-N 0.000 claims 1
239000004480 active ingredient Substances 0.000 claims 1
230000000202 analgesic effect Effects 0.000 claims 1
239000000812 cholinergic antagonist Substances 0.000 claims 1
239000000178 monomer Substances 0.000 claims 1
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VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
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CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
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